3-Nitrobenzaldehyde → HCID 13108116, compound

HRID 544248Notes

Reaction equation

HRID 544248 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[NH2:12]/[C:13](/[CH3:19])=[CH:14]\[C:15]([O:17][CH3:18])=[O:16].[C:20]([N:28]1[CH2:33][CH2:32][CH:31]([O:34][C:35](=[O:40])[CH2:36][C:37]([CH3:39])=O)[CH2:30][CH2:29]1)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1>[CH3:18][O:17][C:15]([C:14]1[CH:7]([C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:36]([C:35]([O:34][CH:31]2[CH2:32][CH2:33][N:28]([C:20](=[O:27])[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:29][CH2:30]2)=[O:40])=[C:37]([CH3:39])[NH:12][C:13]=1[CH3:19])=[O:16]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 20459844HCID 20459844, compound

Product 1

HCID 13108116HCID 13108116, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In this example, 2.74 g of m-nitrobenzaldehyde, 2.09 g of methyl β-aminocrotonate and 5.50 g of acetoacetic acid-N-benzoyl-4-piperidinyl ester obtained in Reference Example 3 (hereinafter described) were added to 10 ml of THF, and stirring was effected at reflux for 33 hours. The reaction mixture was treated similarly as in Example 1 to obtain 2.84 g of 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid-3-(N-benzoyl-4-piperidinyl) ester-5-methyl ester [compound of the general formula (I) wherein R1 =R2 =R4 =CH3, ##STR14## wherein n=0, ##STR15## (yield: 30.2%)

Workup

  1. temperatureat reflux for 33 hours
  2. additionThe reaction mixture was treated similarly as in Example 1

Sources & evidence

ORD record
ord-e5baa371d242454d8cad0b5e083b8210
Source dataset
uspto-grants-1984_05
Patent number
US04448964

Reaction notes

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