Acetyl chloride → Methyl 3-Amino-4-chlorobenzoate

HRID 272561

反応式

HRID 272561 の反応式
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[NH2:11].[C:12](Cl)(=O)C>CO>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:12])=[O:7])=[CH:4][C:3]=1[NH2:11]

参加物

4

反応物 2

HCID 6367Acetyl chlorideHCID 760923-Amino-4-chlorobenzoic acid

生成物 1

HCID 593055Methyl 3-Amino-4-chlorobenzoate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
70 °C

実験手順

To a solution of 4-chloro-3-amino-benzoic acid (10.0 g, 58.3 mmol) in methanol (50 mL) was added acetyl chloride (13.0 mL) dropwise at room temperature. After the addition, the reaction mixture was heated at 70° C. for 3 h and then cooled to room temperature. The solvent was removed under reduced pressure and water (100 mL) was added. The resulting solution was neutralized with NaHCO3 followed by extraction with EtOAc (3×100 mL). The combined organic layers were dried (MgSO4) and concentrated in vacuum to afford a yellow oil (22, 10.5 g, 97%). 1H NMR (DMSO-d6, 300 MHz) δ 7.41 (??d, J=2.1 Hz, 1H), 7.31 (d, J=8.4 Hz, 1H), 7.09 (dd, J=2.1, 8.4 Hz, 1H), 5.66 (br s, 2H), 3.80 (s, 3H).

後処理

  1. additionAfter the addition
  2. temperaturecooled to room temperature
  3. customThe solvent was removed under reduced pressure and water (100 mL)
  4. additionwas added
  5. extractionfollowed by extraction with EtOAc (3×100 mL)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. concentrationconcentrated in vacuum
  8. customto afford a yellow oil (22, 10.5 g, 97%)

出典と根拠

ORDレコード
ord-0cee1c864a20495cba821184f621b338
出典データセット
uspto-grants-2008_11
特許番号
US07456178B2

関連ノート

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