Piperonal → Methyl 4-(1,3-benzodioxol-5-yl)-1,2-dihydro-6-ethoxy-1-(2-methoxybenzyl)-2-oxoquinoline-3-carboxylate

HRID 2907

반응식

HRID 2907 반응식
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5]Cl.[O:11]1[C:15]2[CH:16]=[CH:17][C:18]([C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([O:30][CH2:31][CH3:32])[CH:28]=4)[NH:23][C:22](=[O:33])[C:21]=3[C:34]([O:36][CH3:37])=[O:35])=[CH:19][C:14]=2[O:13][CH2:12]1.NC1C=CC(OCC)=CC=1C(=O)C1C=CC2OCOC=2C=1.ClC(CC(OC)=O)=O.C1OC2C=CC(C=O)=CC=2O1.C(OC(NC1C=CC(OCC)=CC=1)=O)(C)(C)C.C([Li])(C)(C)C>ClCCl.C(N(C(C)C)C(C)C)C.C[O-].[Na+].C1COCC1.CN(C=O)C.C(=O)([O-])[O-].[K+].[K+]>[O:11]1[C:15]2[CH:16]=[CH:17][C:18]([C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([O:30][CH2:31][CH3:32])[CH:28]=4)[N:23]([CH2:5][C:4]4[CH:7]=[CH:8][CH:9]=[CH:10][C:3]=4[O:2][CH3:1])[C:22](=[O:33])[C:21]=3[C:34]([O:36][CH3:37])=[O:35])=[CH:19][C:14]=2[O:13][CH2:12]1

참가 물질

14

반응물 7

HCID 8438PiperonalHCID 814952-(Chloromethyl)anisoleHCID 123460Methyl malonyl chlorideHCID 4935448Tert-butyl 4-ethoxyphenylcarbamateHCID 189361681-Amino-2-(3,4-methylenedioxybenzoyl)-4-ethoxybenzene2회HCID 53948070Methyl 4-(1,3-benzodioxol-5-yl)-1, 2-dihydro-6-ethoxy-2-oxoquinoline-3-carboxylateHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 9913328Methyl 4-(1,3-benzodioxol-5-yl)-1,2-dihydro-6-ethoxy-1-(2-methoxybenzyl)-2-oxoquinoline-3-carboxylate

시약·촉매·용매 6

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매2회HCID 8028Tetrahydrofuran용매HCID 11430Potassium Carbonate용매HCID 81531Diisopropylethylamine용매HCID 10942334Sodium Methoxide용매

실험 절차

A 50% solution of 0.4 g of 2-methoxybenzyl chloride ("A") in dichloromethane is added to a solution of 0.4 g of methyl 4-(1,3-benzodioxol-5-yl)-1, 2-dihydro-6-ethoxy-2-oxoquinoline-3-carboxylate (obtainable by reacting 1-amino-2-(3,4-methylenedioxybenzoyl)-4-ethoxybenzene and methyl chloroformylacetate in dichloromethane and ethyldiisopropylamine with subsequent cyclization of the intermediate in sodium methanolate solution, m.p. 224°-225°; 1-amino-2-(3,4-methylenedioxybenzoyl)-4-ethoxybenzene is obtainable by reacting 3,4-methylenedioxybenzaldehyde and N-(tert-butyloxycarbonyl)-p-ethoxyaniline, m.p. 113°-114°, in THF, tert-butyllithium at -78°, subsequently oxidizing the resulting 3', 4'-methylenedioxy-2-(N-tert-butyloxy-carbonylamino)-5-ethoxydiphenylmethanol and eliminating the amino protective group, EI-MS 285) in 5 ml of DMF and 0.17 g of potassium carbonate. The reaction mixture is stirred for 4 hours and worked up as usual. This results in the N-alkylation product methyl 4-(1,3-benzodioxol-5-yl)-1,2-dihydro-6-ethoxy-1-(2-methoxybenzyl)-2-oxoquinoline-3-carboxylate, m.p. 182°-183° and the -alkylation product methyl 4-(1,3-benzodioxol-5-yl)-6-ethoxy-2-(2-methoxybenzyloxy) quinoline-3-carboxy-late, m.p. 157°-158°.

후처리

  1. customat -78°

출처 및 근거

ORD 기록
ord-e9dbcb3fceb74a8f85be0773e105b776
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05731321

연결된 노트

불러오는 중…