Formic Acid → HCID 13376540, compound

HRID 1979680Notes

Reaction equation

HRID 1979680 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][N:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[NH2:12])([O-:3])=[O:2].[CH:19](O)=[O:20]>>[CH:19]([NH:12][N:11]([CH2:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:20]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 3229111-[(2-nitrophenyl)methyl]-1-phenylhydrazine

Product 1

HCID 13376540HCID 13376540, compoundYield 81.8%

Procedure

A stirred solution of 48.66 g (0.2 mol) of 1-[(2-nitrophenyl)methyl]-1-phenylhydrazine and 200 ml of 97% formic acid solution was heated 4 hours under reflux and allowed to stand overnight (about 16 hours) at ambient temperature. Excess formic acid was removed on a rotary evaporator and the residue was dissolved in 1500 ml of CH2Cl2. The solution was washed with 10% NaOH and concentrated to dryness. Recrystallization from 600 ml of 95% ethanol afforded 44.0 g (81.8%) of 2-formyl-1-[(2-nitrophenyl)methyl]-1-phenylhydrazine, m.p. 140°-142.5° C.

Workup

  1. temperatureunder reflux
  2. custom(about 16 hours)
  3. customat ambient temperature
  4. customExcess formic acid was removed on a rotary evaporator
  5. dissolutionthe residue was dissolved in 1500 ml of CH2Cl2
  6. washThe solution was washed with 10% NaOH
  7. concentrationconcentrated to dryness
  8. customRecrystallization from 600 ml of 95% ethanol

Sources & evidence

ORD record
ord-8824c9eeeb65407e88a775f8c14a3776
Source dataset
uspto-grants-1984_11
Patent number
US04482547

Reaction notes

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