4-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotoluene → 1-Propanol, 3-[[2-nitro-4-(trifluoromethyl)phenyl]amino]-

HRID 1833612Notes

Reaction equation

HRID 1833612 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[NH2:15][CH2:16][CH2:17][CH2:18][OH:19]>C(O)CCC>[N+:12]([C:3]1[CH:4]=[C:5]([C:8]([F:11])([F:10])[F:9])[CH:6]=[CH:7][C:2]=1[NH:15][CH2:16][CH2:17][CH2:18][OH:19])([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 84624-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotolueneHCID 90863-Amino-1-propanol

Product 1

HCID 28475091-Propanol, 3-[[2-nitro-4-(trifluoromethyl)phenyl]amino]-Yield 100%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 100 parts of 1-chloro-2-nitro-4-(trifluoromethyl)benzene, 90 parts of 3-amino-1-propanol and 200 parts of butanol is stirred and heated till reflux. Stirring at reflux is continued overnight. The reaction mixture is cooled and evaporated. Water is added to the residue and the whole is acidified with a hydrochloric acid solution. The product is extracted with methylbenzene. The extract is dried, filtered and evaporated. The solid residue is crystallized from petroleumether. The product is filtered off and dried, yielding 141 parts (100%) of 3-{[2-nitro-4-(trifluoromethyl)phenyl]amino}-1-propanol.

Workup

  1. temperatureheated
  2. temperaturetill reflux
  3. stirringStirring
  4. temperatureat reflux
  5. temperatureThe reaction mixture is cooled
  6. customevaporated
  7. additionWater is added to the residue
  8. extractionThe product is extracted with methylbenzene
  9. customThe extract is dried
  10. filtrationfiltered
  11. customevaporated
  12. customThe solid residue is crystallized from petroleumether
  13. filtrationThe product is filtered off
  14. customdried

Sources & evidence

ORD record
ord-dab44518a0314acf93f5f7b15750a90c
Source dataset
uspto-grants-1978_01
Patent number
US04066772

Reaction notes

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