Hydrochloric Acid → Ethyl 3-(aminomethyl)-6-chloro-2-fluorobenzoate

HRID 508831노트

반응식

HRID 508831 반응식
[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([F:13])[C:5]([CH:14]=[N:15]O)=[CH:4][CH:3]=1.Cl>CO.[Zn]>[NH2:15][CH2:14][C:5]1[C:6]([F:13])=[C:7]([C:2]([Cl:1])=[CH:3][CH:4]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9]

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 76800184Ethyl 6-chloro-2-fluoro-3-((hydroxyimino)methyl)benzoate

생성물 1

HCID 58483233Ethyl 3-(aminomethyl)-6-chloro-2-fluorobenzoate수율 79.5%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 887Methanol용매

반응 조건

온도
60 °C

실험 절차

To a solution of ethyl 6-chloro-2-fluoro-3-((hydroxyimino)methyl)benzoate (0.800 g, 3.26 mmol) in MeOH (5 mL) was added Zn (0.850 g, 13.06 mmol), followed by dropwise addition of conc. HCl (catalytic) and the reaction mixture was heated at 60° C. for 2-3 h. Excess of solvent was removed under vacuum and the residue was diluted with water and basified with NaHCO3, extracted with EtOAc and concentrated to afford 0.600 g of the product. 1H NMR (300 MHz, DMSO d6): δ 1.31 (t, J=7.2 Hz, 3H), 3.76 (s, 2H), 4.38 (q, J=6.9 Hz, 2H), 7.41 (d, J=8.1 Hz, 1H), 7.65 (t, J=8.1 Hz, 1H).

후처리

  1. customExcess of solvent was removed under vacuum
  2. additionthe residue was diluted with water
  3. extractionextracted with EtOAc
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-021ec19d312e4e1f9b4eb7039ee5d178
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096545B2

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