3-Nitrobenzaldehyde → HCID 15718252, compound

HRID 2107960Notes

Reaction equation

HRID 2107960 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].[C:12]([O:18][CH2:19][C:20]([CH3:36])([CH3:35])[CH2:21][N:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]1)(=[O:17])[CH2:13][C:14]([CH3:16])=O.[NH2:37]/[C:38](/[CH3:44])=[CH:39]\[C:40]([O:42][CH3:43])=[O:41]>C(O)(C)C>[CH3:16][C:14]1[NH:37][C:38]([CH3:44])=[C:39]([C:40]([O:42][CH3:43])=[O:41])[CH:7]([C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:13]=1[C:12]([O:18][CH2:19][C:20]([CH3:35])([CH3:36])[CH2:21][N:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:32])[CH3:33])=[O:29])[CH2:24][CH2:23]1)=[O:17]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 15718278HCID 15718278, compound

Product 1

HCID 15718252HCID 15718252, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1.6 g of m-nitrobenzaldehyde, 3.7 g of 3-[4-(tert-butyloxycarbonyl)-1-piperazinyl]-2,2-dimethylpropyl acetoacetate, and 1.3 g of methyl 3-aminocrotonate were dissolved in 10 ml of isopropanol, and the solution was subjected to heating reflux for 12 hours. Then, the solvent was concentrated under reduced pressure. Diethyl ether was added to the residue to give 2.7 g of a colorless powdery crystal (yield: 44%). The IR and NMR data of the compound thus obtained are as follows: ##STR14##

Workup

  1. temperatureto heating
  2. temperaturereflux for 12 hours
  3. concentrationThen, the solvent was concentrated under reduced pressure
  4. additionDiethyl ether was added to the residue

Sources & evidence

ORD record
ord-0bce222722ad42d2b7198e966ce6eace
Source dataset
uspto-grants-1990_06
Patent number
US04937242

Reaction notes

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