Sodium Hydroxide → 2-(Trifluoromethyl)-1,4-phenyldiamine

HRID 982457Notes

Reaction equation

HRID 982457 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[OH-].[Na+]>C(O)C.[Zn]>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 671284-Nitro-alpha,alpha,alpha-trifluoro-o-toluidine

Product 1

HCID 1361972-(Trifluoromethyl)-1,4-phenyldiamineYield 95.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

2-Amino-5-nitrobenzotrifluoride (51.6 g, 0.25 mole), manufactured by Marshallton Research Laboratories, Inc., was dissolved in 95% aqueous ethanol (100 ml) and 25% aqueous sodium hydroxide solution (20 ml) and was heated to gentle reflux. Zinc dust (65 g, 1.00 g atom) was added slowly (50 minutes) at a rate to maintain reflux without external heating. After one hour, the mixture was filtered hot and the filter cake was extracted with two 75 ml portions of hot ethanol. The filtrate, combined with the washings, was concentrated under vacuum producing dark crystals (42 g, 95% yield). These were recrystallized from methanol/methylene chloride.

Workup

  1. temperatureto maintain
  2. temperaturereflux without external heating
  3. filtrationthe mixture was filtered hot
  4. extractionthe filter cake was extracted with two 75 ml portions of hot ethanol
  5. concentrationwas concentrated under vacuum

Sources & evidence

ORD record
ord-c8506a18226842659e5a8bd872aa6a65
Source dataset
uspto-grants-1991_02
Patent number
US04996278

Reaction notes

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