N-methyl-2-pyrrolidone → 4-(2-Hydroxymethyl-1-pyrrolidinyl)-2-nitrobenzoic acid methyl ester

HRID 917614Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7](Cl)=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12].[NH:15]1[CH2:21][CH2:20][CH2:19][C@H:16]1[CH2:17][OH:18].C(N(C(C)C)CC)(C)C.CN1CCCC1=O>O.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N:15]2[CH2:21][CH2:20][CH2:19][CH:16]2[CH2:17][OH:18])=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-chloro-2-nitrobenzoic acid methyl ester 100 mg, prolinol 56 mg, diisopropylethylamine 90 mg and 1-methyl-2-pyrrolidinone 3 ml is stirred at 100° C. for 13 hours. Ethyl acetate and water are added to the mixture, and the organic layer is washed with water (twice) and brine, and dried over sodium sulfate. After removal of the sodium sulfate, the filtrate is concentrated in vacuo, and the residue is purified with column chromatography (silica gel 100 g, solvent; hexane:ethyl acetate=4:1→2:1→1:1→100% ethyl acetate) to give 4-(2-hydroxymethyl-1-pyrrolidinyl)-2-nitrobenzoic acid methyl ester 1.298 g as a pale yellow viscosity oil. MS(m/z): 285(M+H)+

Workup

washthe organic layer is washed with water (twice) and brine
dry with materialdried over sodium sulfate
customAfter removal of the sodium sulfate
concentrationthe filtrate is concentrated in vacuo
customthe residue is purified with column chromatography (silica gel 100 g, solvent; hexane:ethyl acetate=4:1→2:1→1:1→100% ethyl acetate)

Sources & evidence

ORD record: ord-b2e5fc4e7d4946e9a9e9a2109724dd19
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07273868B2

Reaction notes

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