Diethyl acetylenedicarboxylate → Ethyl 7-butyl-4-oxo-1,4-dihydroquinoline-2-carboxylate

HRID 326609

反応式

HRID 326609 の反応式
[CH2:1]([C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][CH:11]=1)[NH2:8])[CH2:2][CH2:3][CH3:4].[CH2:12]([O:14][C:15]([C:17]#[C:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:16])[CH3:13]>>[CH2:1]([C:5]1[CH:11]=[CH:10][CH:9]=[C:7]2[C:6]=1[C:19](=[O:20])[CH:18]=[C:17]([C:15]([O:14][CH2:12][CH3:13])=[O:16])[NH:8]2)[CH2:2][CH2:3][CH3:4].[CH2:1]([C:5]1[CH:6]=[C:7]2[C:9]([C:15](=[O:16])[CH:17]=[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[NH:8]2)=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4]

参加物

4

反応物 2

HCID 69803Diethyl acetylenedicarboxylateHCID 793333-Butylbenzenamine

生成物 2

HCID 19735204Ethyl 7-butyl-4-oxo-1,4-dihydroquinoline-2-carboxylateHCID 19735225Ethyl 5-butyl-4-oxo-1,4-dihydroquinoline-2-carboxylate

実験手順

Treatment of 3-butylaniline (7 g) with diethylacetylene dicarboxylate (7.5 ml), as described in Example 1b, gave ethyl 5-butyl-4-oxo-1,4-dihydroquinoline-2-carboxylate (0.62 g) mp 132°-133° C., δ (360 MHz, DMSO-d6) 0.89 (3H, t, CH2CH2CH3), 1.36 (5H, m, CO2CH2CH3 and CH2CH2CH3), 1.47 (2H, m, CH2CH2CH2), 3.25 (2H, t, CH2CH2CH2CH3), 4.41 (2H, q, CO2CH2), 6.55 (1H, s, 3-H), 7.04 (1H, d, 8-H), 7.52 (1H, t, 7-H) 7.80 (1H, d, 6-H) and 11.75 (1H, bs, NH) and ethyl 7-butyl-4-oxo-1,4-dihydroquinoline-2-carboxylate (1.78 g), mp 124°-126° C., δ (360 MHz, DMSO-d6) 0.91 (3H, t, CH2CH2CH3), 1.36 (5H, m, CO2CH2CH3 and CH2CH2CH3), 1.61 (2H, m, CH2CH2CH2), 2.70 (2H, t, CH2CH2CH2), 4.40 (2H, q, CO2CH2), 6.62 (1H, s, 3-H), 7.21 (1H, d, 6-H), 7.75 (1H, s, 8-H), 7.98 (1H, d, 5-H) and 11.87 (1H, bs, NH).

出典と根拠

ORDレコード
ord-89ec6300b7fd432b82589cc9c0e8fef1
出典データセット
uspto-grants-1993_12
特許番号
US05270309

関連ノート

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