Acetyl chloride → Methyl 3-Amino-4-chlorobenzoate

HRID 272561

반응식

HRID 272561 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 593055Methyl 3-Amino-4-chlorobenzoate

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
70 °C

실험 절차

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).

후처리

  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%)

출처 및 근거

ORD 기록
ord-0cee1c864a20495cba821184f621b338
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456178B2

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