3-methoxy-2-nitrobenzoic acid -Drug Synthesis Database

【结构式】

【分子编号】25827

【品名】3-methoxy-2-nitrobenzoic acid

【CA登记号】4920-80-3

【分子式】C₈H₇NO₅

【分子量】197.14732

【元素组成】C 48.74% H 3.58% N 7.1% O 40.58%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(II)

In an alternative procedure, 3-methoxy-2-nitrobenzoic acid (II) was treated with SOCl2 in the presence of DMF in THF, and the resulting acid chloride (III) was converted to amide (IV) with aqueous ammonia. Catalytic hydrogenation of (IV) over Pd/C produced aniline (V), which was then acetylated with AcCl and pyridine. The crude acetylamino compound (VI) was cyclized by treatment with aqueous NaOH to yield the quinazolinone (VII). Finally, demethylation of the methoxy group of (VII) with BBr3 provided the required 8-hydroxyquinazolinone.

参考文献中间体

合成目标

【1】 Griffin, R.J.; Srinivasan, S.; Bowman, K.; Calvert, A.H.; Curtin, N.J.; Newell, D.R.; Pemberton, L.C.; Golding, B.T.; Resistance-modifying agents. 5. Synthesis and biological properties of quinazolinone inhibitors of the DNA repair enzyme poly(ADP-ribose) polymerase (PARP). J Med Chem 1998, 41, 26, 5247.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	19273	acetyl chloride	75-36-5	C₂H₃ClO	详情	详情
(II)	25827	3-methoxy-2-nitrobenzoic acid	4920-80-3	C₈H₇NO₅	详情	详情
(III)	25828	3-methoxy-2-nitrobenzoyl chloride		C₈H₆ClNO₄	详情	详情
(IV)	25829	3-methoxy-2-nitrobenzamide		C₈H₈N₂O₄	详情	详情
(V)	25830	2-amino-3-methoxybenzamide		C₈H₁₀N₂O₂	详情	详情
(VI)	25831	2-(acetamido)-3-methoxybenzamide		C₁₀H₁₂N₂O₃	详情	详情
(VII)	25832	8-methoxy-2-methyl-4(3H)-quinazolinone		C₁₀H₁₀N₂O₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

Treatment of 3-methoxy-2-nitrobenzoic acid (I) with oxalyl chloride gave the corresponding acid chloride (II), which was then coupled with 2-amino-5-chloropyridine (III) to yield amide (IV). The reduction of the nitro group of (IV) using sodium hydrosulfite afforded aniline (V). Further chlorination of (V) with N-chlorosuccinimide furnished the 5-chloro derivative (VI).

参考文献中间体

合成目标

【1】 Cheeseman, S.; Chou, Y.-L.; Ye, B.; et al.; Design, synthesis, and biological activity of novel non-amidine factor Xa inhibitors, 4: Optimization of hydrophilic substituents for potency and oral availability. 221st ACS Natl Meet (April 1 2001, San Diego) 2001, Abst MEDI 128.
【2】 Snider, R.M.; Liang, A.M.; Wu, S.C.; Arnaiz, D.O.; Sacchi, K.L.; Kochanny, M.J.; Phillips, G.B.; Ye, B.; Zhao, Z.; Morrissey, M.M.; Griedel, B.D.; Lee, W.; Sakata, S.T.; Karanjawala, R.E.; Chou, Y.-L.; Shaw, K.J. (Schering AG); Ortho-anthranilamide derivs. as anticoagulants. EP 1040108; JP 2001526283; US 6140351; WO 9932477 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	25827	3-methoxy-2-nitrobenzoic acid	4920-80-3	C₈H₇NO₅	详情	详情
(II)	25828	3-methoxy-2-nitrobenzoyl chloride		C₈H₆ClNO₄	详情	详情
(III)	18559	5-Chloro-2-pyridinylamine; 5-Chloro-2-pyridinamine; 2-Amino-5-chloropyridine	1072-98-6	C₅H₅ClN₂	详情	详情
(IV)	51186	N-(5-chloro-2-pyridinyl)-3-methoxy-2-nitrobenzamide		C₁₃H₁₀ClN₃O₄	详情	详情
(V)	51187	2-amino-N-(5-chloro-2-pyridinyl)-3-methoxybenzamide		C₁₃H₁₂ClN₃O₂	详情	详情
(VI)	51188			C₁₃H₁₁Cl₂N₃O₂	详情	详情

Extended Information