Methanol → Methyl 3-aminobenzoate hydrochloride

HRID 37775

반응식

HRID 37775 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].S(Cl)([Cl:13])=O.[CH3:15]O>>[ClH:13].[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH3:15])=[O:6]

참가 물질

4

반응물 3

HCID 887MethanolHCID 74193-Aminobenzoic AcidHCID 24386Thionyl Chloride

생성물 1

HCID 12238913Methyl 3-aminobenzoate hydrochloride수율 98%

실험 절차

To a suspension of 3-aminobenzoic acid (1.03 g mg, 7.52 mmol) in MeOH (80 mL) at 0° C. was added dropwise thionyl chloride (5 mL). The resulting solution was allowed to stir for 16 h before the solvent was removed by evaporation and the product precipitated with diethyl ether. The diethyl ether was removed by evaporation to yield the title compound (1.38 g, 7.38 mmol, 98%) as a white solid. Mp 176-178° C. 1H NMR (D2O, 300 MHz): δ 7.75 (dt, J=1.8, 3.3, 7.2 Hz, 1H, ArH); 7.71 (m, 1H, ArH); 7.42 (m, 1H, ArH); 7.37 (m, 1H, ArH); 3.66 (s, 31H, OCH3). Mass Spectrum (C1) m/z 152 (100%) [M+]. HRMS calcd for C8H10NO2 152.0712, found 152.0698.

후처리

  1. customwas removed by evaporation
  2. customthe product precipitated with diethyl ether
  3. customThe diethyl ether was removed by evaporation

출처 및 근거

ORD 기록
ord-1b2668063c35463880a13e4b955aea22
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524657B2

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