Quinone → HCID 615240, compound

HRID 986812Notes

Reaction equation

HRID 986812 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[NH2:11].[O:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[CH:17]=O.C1(=O)C=CC(=O)C=C1>CC(O)C.O>[O:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17]1[NH:11][C:3]2[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=2[N:1]=1

Participants

6

Reactant 3

HCID 4650QuinoneHCID 7362FurfuralHCID 51117914-Nitro-1,2-phenylenediamine

Product 1

HCID 615240HCID 615240, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A mixture of 1,2-diamino-4-nitrobenzene (31 g, 0.2 mol) and 2-furancarboxaldehyde (25 g, 0.26 mol) in 2-propanol is treated with p-benzoquinone (24 g, 0.22 mol). The reaction mixture is heated under reflux for 2 h. The reaction solution is diluted with water to precipitate the product. After drying, the crude product weighs 46 g (100%). Recrystllization from nitromethane provides an analytical sample which melts at 228°-229° C. Anal. Calcd for C11H7N3O3 ; C, 57.64; H, 3.08; N, 18.34. Found: C, 57.55; H, 3.04; N, 18.53.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 2 h
  3. customto precipitate the product
  4. customAfter drying
  5. customRecrystllization from nitromethane provides an analytical sample which melts at 228°-229° C

Sources & evidence

ORD record
ord-df39ae7c9c2c4e3e9ca51dcf6dd765f1
Source dataset
uspto-grants-1987_12
Patent number
US04716168

Reaction notes

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