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

HRID 59338ノート

反応式

HRID 59338 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 887Methanol溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-5924e4964a654ca3a9e2ef8650204359
出典データセット
uspto-grants-2016_09
特許番号
US09439890B2

反応ノート

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