3-Nitrobenzaldehyde → Nimodipine

HRID 845572

反応式

HRID 845572 の反応式
[C:1]([O:7][CH2:8][CH2:9][O:10][CH3:11])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[NH2:12]/[C:13](/[CH3:21])=[CH:14]\[C:15]([O:17][CH:18]([CH3:20])[CH3:19])=[O:16].[N+:22]([C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH:28]=O)([O-:24])=[O:23]>CC(O)C.ClCCl>[CH3:5][C:3]1[NH:12][C:13]([CH3:21])=[C:14]([C:15]([O:17][CH:18]([CH3:20])[CH3:19])=[O:16])[CH:28]([C:27]2[CH:30]=[CH:31][CH:32]=[C:25]([N+:22]([O-:24])=[O:23])[CH:26]=2)[C:2]=1[C:1]([O:7][CH2:8][CH2:9][O:10][CH3:11])=[O:6]

参加物

6

反応物 3

HCID 74493-NitrobenzaldehydeHCID 897342-Methoxyethyl acetoacetateHCID 111372742-Butenoic acid, 3-amino-, 1-methylethyl ester

生成物 1

HCID 4497Nimodipine収率 58%

試薬・触媒・溶媒 2

HCID 3776Isopropanol溶媒HCID 6344Dichloromethane溶媒

実験手順

A solution of 2-methoxyethyl acetoacetate (51) (32 g, 0.2 mol), 1-methylethyl 3-aminocrotonate (52) (28.8 g, 0.2 mol) and 3-nitrobenzaldehyde (30.6 g, 0.2 mol) in 2-propanol (280 mL) was refluxed for 9 h. The mixture was diluted with dichloromethane (1000 mL) and dried (MgSO4), and the solvent was removed with a rotary evaporator. The crude produce was recrystallized from ethyl acetate-petroleum ether to afford 48 g (0.115 mol, 58%) of 50 as a yellow crystalline solid: mp 122°-123° C. (lit.81 mp 125° C.); IR (CH2Cl2) 3440, 2975, 1692, 1620, 1530, 1460, 1345, 1210, 1095 cm-1 ; 1H NMR (CDCl3) δ 1.08 (d, J=6.2 Hz, 3H), 1.25 (d, J=6.2 Hz, 3H), 2.33 (s, 6H), 3.33 (s, 3H), 3.55 (t, J=4.8 Hz, 2H), 4.12-4.20 (m, 2H), 4.93 (septet, J=6.2 Hz, 1H), 5.09 (s, 1H), 6.31 (s, 1H), 7.34-8.13 (m, 4H); 13C NMR (CDCl3) δ 19.38, 19.53, 21.85, 22.17, 40.14, 58.90, 63.05, 67.43, 70.58, 102.93, 103.75, 121.36, 123.33, 128.70, 134.81, 144.84, 145.62, 148.16, 150.20, 166.75, 167.26.

後処理

  1. dry with materialdried (MgSO4)
  2. customthe solvent was removed with a rotary evaporator
  3. customThe crude produce
  4. customwas recrystallized from ethyl acetate-petroleum ether

出典と根拠

ORDレコード
ord-6bd42e4dc226461895cbf9de5611e948
出典データセット
uspto-grants-1988_07
特許番号
US04758669

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