Oxalyl chloride → 6-chloro-4-(3-hydroxyphenyl)-3-(3-methyl-isoxazol-5-yl)-1H-quinolin-2-one

HRID 2053423ノート

反応式

HRID 2053423 の反応式
[NH2:1][C:2]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([OH:12])[CH:7]=1)=O.[CH3:18][C:19]1[CH:23]=[C:22]([CH2:24][C:25](Cl)=[O:26])[O:21][N:20]=1.Cl.CC1C=C(CC(O)=O)ON=1.C(Cl)(=O)C(Cl)=O>C(Cl)Cl.C(N(CC)CC)C.CN(C)C=O>[Cl:17][C:14]1[CH:13]=[C:3]2[C:2](=[CH:16][CH:15]=1)[NH:1][C:25](=[O:26])[C:24]([C:22]1[O:21][N:20]=[C:19]([CH3:18])[CH:23]=1)=[C:4]2[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([OH:12])[CH:7]=1

参加物

8

反応物 4

HCID 65578Oxalyl chlorideHCID 2794900(2-Amino-5-chlorophenyl)(3-hydroxyphenyl)methanoneHCID 123668732-(3-Methylisoxazol-5-yl)acetyl chlorideHCID 67010666(3-Methyl-isoxazol-5-yl)-acetic acid hydrochloride

生成物 1

HCID 1354970676-chloro-4-(3-hydroxyphenyl)-3-(3-methyl-isoxazol-5-yl)-1H-quinolin-2-one収率 70.2%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回HCID 8471Triethylamine溶媒

実験手順

A mixture of 2-amino-5-chloro-3′-hydroxybenzophenone (0.1 g, 0.4 mmol), (3-methyl-isoxazol-5-yl)-acetyl chloride (1.18 mmol) [synthesized from the reaction between (3-methyl-isoxazol-5-yl)-acetic acid hydrochloride and oxalyl chloride catalyzed by N,N-dimethylformamide in DCM], triethylamine (Et3N) (0.20 mL) and DCM (10 mL) was heated to reflux overnight. The mixture was then cooled to room temperature and concentrated, and the residue was purified by flash chromatography on silica gel (5% methanol in DCM) to give 6-chloro-4-(3-hydroxyphenyl)-3-(3-methyl-isoxazol-5-yl)-1H-quinolin-2-one (99 mg, 70%). 1H NMR (300 MHz, DMSO-d6) δ 9.68 (s, 1H), 7.68-7.60 (m, 2H), 7.43 (d, J=10.0 Hz, 1H), 7.25 (t, J=10.0 Hz, 1H), 7.01-6.97 (m, 1H), 6.88-6.80 (m, 1H), 6.68-6.59 (m, 1H), 6.47 (s, 1H), 2.15 (s, 3H). MS: 353.2 (M+H).

後処理

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated
  4. customthe residue was purified by flash chromatography on silica gel (5% methanol in DCM)

出典と根拠

ORDレコード
ord-c15a2c0a8f134028be82db83641f9d26
出典データセット
uspto-grants-2008_02
特許番号
US07326788B2

反応ノート

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