3-Nitrobenzaldehyde → HCID 86745039, compound

HRID 728320Notes

Reaction equation

HRID 728320 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][CH2:20][NH:21][C:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1)(=[O:17])[CH2:13][C:14]([CH3:16])=O.[NH2:30]/[C:31](/[CH3:43])=[CH:32]\[C:33]([O:35][CH2:36][CH2:37][CH2:38][O:39][N+:40]([O-:42])=[O:41])=[O:34].C([O-])(=O)C.[NH2+]1CCCCC1>CC(O)C>[N:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:22]([NH:21][CH2:20][CH2:19][O:18][C:12]([C:13]1[CH:7]([C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:32]([C:33]([O:35][CH2:36][CH2:37][CH2:38][O:39][N+:40]([O-:42])=[O:41])=[O:34])=[C:31]([CH3:43])[NH:30][C:14]=1[CH3:16])=[O:17])=[O:29]

Participants

6

Reactant 4

HCID 74493-NitrobenzaldehydeHCID 3014295Piperidinium acetateHCID 10465498HCID 10465498, compoundHCID 15662249HCID 15662249, compound

Product 1

HCID 86745039HCID 86745039, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 9.07 g (0.06 mole) of m-nitrobenzaldehyde, 15.00 g (0.06 mole) of 2-picolinoylaminoethyl acetoacetate, 12.24 g (0.06 mole) of 3-nitrooxypropyl 3-aminocrotonate and 1.74 g (0.012 mole) of piperidinium acetate in 200 ml of 2-propanol was refluxed for 4 hours. After the reaction, the solvent was evaporated, and the residue was purified by silica gel column chromatography [eluent; ethyl acetate hexane (1:3)] to give 20.45 g of the title compound.

Workup

  1. customAfter the reaction
  2. customthe solvent was evaporated
  3. customthe residue was purified by silica gel column chromatography [eluent; ethyl acetate hexane (1:3)]

Sources & evidence

ORD record
ord-a2ebb0cc5837469496b07f51d9c1946d
Source dataset
uspto-grants-1991_09
Patent number
US05047543

Reaction notes

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