Ethyl Acetate → 3-Amino-2-(3-methoxy-benzoyl)-7,8-dihydro-6H-naphtho[2,3-b]furan-5-one

HRID 856950

反応式

HRID 856950 の反応式
[OH:1][C:2]1[C:3]([C:13]#[N:14])=[CH:4][C:5]2[C:6](=[O:12])[CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=1)[C:20](=[O:23])[CH2:21]Br.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[NH2:14][C:13]1[C:3]2[CH:4]=[C:5]3[C:10]([CH2:9][CH2:8][CH2:7][C:6]3=[O:12])=[CH:11][C:2]=2[O:1][C:21]=1[C:20](=[O:23])[C:19]1[CH:24]=[CH:25][CH:26]=[C:17]([O:16][CH3:15])[CH:18]=1

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 101294Bromomethyl 3-methoxyphenyl ketoneHCID 218649643-Hydroxy-8-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

生成物 1

HCID 218649513-Amino-2-(3-methoxy-benzoyl)-7,8-dihydro-6H-naphtho[2,3-b]furan-5-one収率 24%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

To a solution of 3-hydroxy-8-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile from method II-6 (45 mg, 0.24 mmol) and 3-methoxyphenacyl bromide (60 mg, 0.26 mmol, 1.1 eq) in anhydrous N,N-dimethylformamide (2 mL) was added potassium carbonate (66 mg, 0.48 mmol, 2 eq). The reaction mixture was shaken at 90° C. for 17 h. The mixture was cooled to room temperature and poured into ethyl acetate and water. The aqueous layer was extracted with ethyl acetate twice. Combined the organic layers and evaporated in vacuo. The crude product was washed with methanol and gave 19 mg (24%) of 3-Amino-2-(3-methoxy-benzoyl)-7,8-dihydro-6H-naphtho[2,3-b]furan-5-one as a yellow solid. 1H-NMR (DMSO-d6) δ 8.72 (s, 1H), 7.68 to 7.42 (m, 5H), 7.18 to 7.14 (m, 1H), 6.33 (s, 1H), 3.84 (s, 3H), 3.07 (t, J=6.0 Hz, 2H), 2.65 (t, J=6.6 Hz, 2H), 2.50 (m, 2H); MS LC-MS (MH+=336.2); Rf=0.62, 50% ethyl acetate-hexane.

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. extractionThe aqueous layer was extracted with ethyl acetate twice
  3. customevaporated in vacuo
  4. washThe crude product was washed with methanol

出典と根拠

ORDレコード
ord-b868b18ce04b49debaae6542a54a2db7
出典データセット
uspto-grants-2006_12
特許番号
US07144885B2

関連ノート

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