Methanol → Methyl 3-aminobenzoate hydrochloride

HRID 37775

反応式

HRID 37775 の反応式
[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]

参加物

4

反応物 3

HCID 887MethanolHCID 74193-Aminobenzoic AcidHCID 24386Thionyl Chloride

生成物 1

HCID 12238913Methyl 3-aminobenzoate hydrochloride収率 98%

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-1b2668063c35463880a13e4b955aea22
出典データセット
uspto-grants-2013_09
特許番号
US08524657B2

関連ノート

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