3-Nitrobenzaldehyde → HCID 15632018, compound

HRID 1087152Notes

Reaction equation

HRID 1087152 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[N+:14]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=O)([O-:16])=[O:15].[NH2:25]/[C:26](/[CH3:32])=[CH:27]\[C:28]([O:30][CH3:31])=[O:29]>C(O)(C)C>[CH3:32][C:26]1[NH:25][C:4]([CH3:5])=[C:3]([C:2]([O:7][CH2:8]/[CH:9]=[CH:10]/[C:11]2[CH:12]=[CH:13][C:8]([O:7][CH:2]3[CH2:3][CH2:4][CH2:5][CH2:6][O:1]3)=[CH:9][CH:10]=2)=[O:1])[CH:20]([C:19]2[CH:22]=[CH:23][CH:24]=[C:17]([N+:14]([O-:16])=[O:15])[CH:18]=2)[C:27]=1[C:28]([O:30][CH3:31])=[O:29]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 1072402H-Pyran, tetrahydro-2-phenoxy-HCID 643918Methyl 3-aminocrotonate

Product 1

HCID 15632018HCID 15632018, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

3.36 Grams of 1-[2(E)-acetoacetocymethylvinyl]-(4-(2-tetrahydropyranyloxy)benzene, 1.5 g of 3-nitrobenzaldehyde and 1.2 g of methyl 3-aminocrotonate were added to 20 ml of isopropanol, and the mixture was refluxed for 8 hours. The reaction mixture was concentrated and the residue was purified by means of a silica gel column chromatography (eluent: chloroform) to yield 1.2 g of methyl 3-(4-tetrahydropyranyloxyphenyl)-2(E)-propenyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-pyridine-3,5-dicarboxylate.

Workup

  1. temperaturethe mixture was refluxed for 8 hours
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by means of a silica gel column chromatography (eluent: chloroform)

Sources & evidence

ORD record
ord-719654ad680e438cb7730f764fd11cf0
Source dataset
uspto-grants-1991_07
Patent number
US05034395

Reaction notes

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