3-Nitrobenzaldehyde → HCID 19894043, compound

HRID 892745Notes

Reaction equation

HRID 892745 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15](=[O:20])[CH2:16][C:17]([CH3:19])=O)[O:4][N:3]=1.[CH3:21][O:22][C:23](=[O:28])/[CH:24]=[C:25](\[NH2:27])/[CH3:26].[N+:29]([C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=1)[CH:35]=O)([O-:31])=[O:30]>C(O)(C)C>[CH3:1][C:2]1[CH:6]=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]([C:16]2[CH:35]([C:34]3[CH:37]=[CH:38][CH:39]=[C:32]([N+:29]([O-:31])=[O:30])[CH:33]=3)[C:24]([C:23]([O:22][CH3:21])=[O:28])=[C:25]([CH3:26])[NH:27][C:17]=2[CH3:19])=[O:20])[O:4][N:3]=1

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 19894041HCID 19894041, compound

Product 1

HCID 19894043HCID 19894043, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

7-(3-methylisoxazol-5-yl)heptylacetoacetate (1.967 g, 0.007 l mol) was added to a solution of methyl-β-aminocrotonate (0.805 g, 0.007 mol) and m-nitrobenzaldehyde (1.057 g, 0.007 mol) in isopropanol (35 mL). The reaction mixture was heated under reflux for 12 h and then concentrated under reduced pressure. The residual oil was purified by elution from a silica gel column using dichloromethane-hexane (9:1, v/v) as eluant to give 3-[7-(3-methylisoxazol-5-yl)heptyloxycarbonyl]-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine (60%) as a pale yellow thick oil. IR (neat) 3330 (NH) and 1701 and 1676 (CO2R)cm-1, NMR (CDCl3) 1.20-1.40 (m, 6H, --(CH2)3), 1.56-1.74 (m, 4H, --(CH2)2), 2.30 (S, 3H, Me), 2.39 (S, 3H, Me), 2.72 (t, J =9 Hz, 2H, CH2 -Het), 3.70 (S, 3H, CO2Me), 3.99-4.16 (m, 2H,--OCH2), 5.14 (S, 1H, H-4), 5.89 (S, 1H, Het-H), 7.06 (S, 1H, NH), 7.38-8.14 (m, 4H, H-2 , H-4', H-5', H-6'). Analysis found: C, 63.48; H, 6.45; N, 7.99. Required: C, 63.39; H, 6.50; N, 8.21 (C27H33N3O7). ##STR6##

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 12 h
  3. concentrationconcentrated under reduced pressure
  4. customThe residual oil was purified by elution from a silica gel column

Sources & evidence

ORD record
ord-21557eee75294436b61b58e36f3ffffd
Source dataset
uspto-grants-1992_06
Patent number
US05120750

Reaction notes

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