Hydrochloric Acid → 2-(Aminomethyl)-5-fluorophenol hydrochloride

HRID 1372273ノート

反応式

HRID 1372273 の反応式
C([O:8][C:9]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:10]=1[C:11]#[N:12])C1C=CC=CC=1.[ClH:18]>C(O)C.C(OCC)(=O)C.[Pd]>[ClH:18].[OH:8][C:9]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:10]=1[CH2:11][NH2:12]

参加物

6

反応物 2

HCID 313Hydrochloric AcidHCID 210698282-(Benzyloxy)-4-fluorobenzonitrile

生成物 1

HCID 210698432-(Aminomethyl)-5-fluorophenol hydrochloride収率 74.3%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of intermediate 134, 2-(benzyloxy)-4-fluorobenzonitrile, (9.03 g, 39.7 mmol) in ethanol (100 mL) and ethyl acetate (100 mL) was stirred with 10% palladium on carbon (1.67 g,) and concentrated hydrochloric acid (12 mL, 144 mmol) under a hydrogen atmosphere (60 psi) for four days. The catalyst was removed by filtration through Celite, and the filtrate was concentrated. The crude product was triturated with ether and the resulting solid collected by filtration to give the title compound (5.24 g, 74% yield) as a pale orange solid. 1H NMR (500 MHz, DMSO-D6) δ ppm: 10.81 (1H, s), 8.18 (3H, s), 7.36 (1H, t, J=7.3 Hz), 6.79 (1H, dd, J=10.8, 2.6 Hz), 6.66 (1H, dt, J=8.5, 2.3 Hz), 3.90 (2H, d, J=5.2 Hz).

後処理

  1. customThe catalyst was removed by filtration through Celite
  2. concentrationthe filtrate was concentrated
  3. customThe crude product was triturated with ether
  4. filtrationthe resulting solid collected by filtration

出典と根拠

ORDレコード
ord-8ccc5eb04d7443c085203606fa80cebc
出典データセット
uspto-grants-2007_01
特許番号
US07157447B2

反応ノート

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