3-Nitroaniline → HCID 76656307, compound

HRID 2061104Notes

Reaction equation

HRID 2061104 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].[C:11]([N:15]=[N:16]/[C:17](/[CH3:24])=[CH:18]\[C:19]([O:21][CH2:22][CH3:23])=[O:20])([O:13][CH3:14])=[O:12].CCCCCC>C1COCC1>[CH2:22]([O:21][C:19](=[O:20])[CH:18]([NH:7][C:6]1[CH:8]=[CH:9][CH:10]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[C:17](=[N:16][NH:15][C:11]([O:13][CH3:14])=[O:12])[CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 74233-NitroanilineHCID 8058HexaneHCID 12438685HCID 12438685, compound

Product 1

HCID 76656307HCID 76656307, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

3-Nitroaniline (2.92 g, 21.27 mmol) was added to a solution of ethyl 3-carbomethoxyazocrotonate (4.2 g, 21.13 mmol) (which is known in the literature) in THF (40 mL), and the mixture was stirred at 70° C. for a day and a night. After cooling to room temperature, hexane was added thereto, and the deposited precipitate was filtered out to yield the title compound (5.08 g, 71%).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe deposited precipitate was filtered out

Sources & evidence

ORD record
ord-fb55e227ec054794a0d7c146af12a434
Source dataset
uspto-grants-2012_10
Patent number
US08278465B2

Reaction notes

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