3',4'-Dimethoxycinnamic acid → 3,4-Dimethoxycinnamoylchloride

HRID 36923

반응식

HRID 36923 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[CH:6]=[CH:7][C:8](O)=[O:9].C(Cl)(=O)C([Cl:19])=O>CN(C=O)C.O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[CH:6]=[CH:7][C:8]([Cl:19])=[O:9]

참가 물질

5

반응물 2

HCID 168483',4'-Dimethoxycinnamic acidHCID 65578Oxalyl chloride

생성물 1

HCID 533992063,4-Dimethoxycinnamoylchloride

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of 3,4-dimethoxycinnamic acid (540 mg), DMF (2 drops) and tetrahydrofuran (10 ml) was added oxalyl chloride (0.27 ml) dropwise. The mixture was stirred at room temperature for 40 minutes, at the end of which time the solvent was distilled off to give 3,4-dimethoxycinnamoyl chloride. The chloride was dissolved in dichloromethane (10 ml) followed by addition of 3-amino-4-(2-methylphenyl)-7,8-dihydrocyclopenta [g] [1]benzopyran-2(6H)-one (582 mg) and N,N-dimethylaniline (0.25 ml). The mixture was then stirred at room temperature for 20 hours, after which it was washed with water, dried (MgSO4) and distilled to remove the solvent. The residue was chromatographed on silica gel and eluted with benzene-acetone (9:1) to give 3-(3,4-dimethoxycinnamoylamino) -4-(2-methylphenyl)-7,8-dihydrocyclopenta[g] 1benzopyran-2(6H)-one as oil. The oil was crystallized from ethanol-isopropyl ether (648 mg, 67.4%). Recrystallization from acetone gave colorless needles, m.p. 159°-160° C.

후처리

  1. distillationwas distilled off

출처 및 근거

ORD 기록
ord-03af43923d334bb58f46283316bba5de
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05418239

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