4-Chloro-3-nitrotoluene → 3-[(4-Methyl-2-nitrophenyl)amino]-1-propanol

HRID 1704450Notes

Reaction equation

HRID 1704450 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[NH2:12][CH2:13][CH2:14][CH2:15][OH:16]>C(O)CCC>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([NH:12][CH2:13][CH2:14][CH2:15][OH:16])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

4

Reactant 2

HCID 69764-Chloro-3-nitrotolueneHCID 90863-Amino-1-propanol

Product 1

HCID 203855403-[(4-Methyl-2-nitrophenyl)amino]-1-propanolYield 33%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 171 parts of 1-chloro-4-methyl-2-nitrobenzene, 150 parts of 3-amino-1-propanol and 400 parts of butanol is stirred and refluxed for 30 hours. The reaction mixture is evaporated and the residue is poured onto water. The product is extracted with methylbenzene. The extract is washed with water and with a hydrochloric acid solution 2N, dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and 5% of methanol as eluent. The pure fractions are collected and the eluent is evaporated, yielding 70 parts (33%) of 3-[(4-methyl-2-nitrophenyl)amino]-1-propanol as a residue.

Workup

  1. temperaturerefluxed for 30 hours
  2. customThe reaction mixture is evaporated
  3. additionthe residue is poured onto water
  4. extractionThe product is extracted with methylbenzene
  5. washThe extract is washed with water and with a hydrochloric acid solution 2N
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is purified by column-chromatography over silica gel using
  10. additiona mixture of trichloromethane and 5% of methanol as eluent
  11. customThe pure fractions are collected
  12. customthe eluent is evaporated

Sources & evidence

ORD record
ord-38d0ddcfcf2c4e7bbe29599e27d0b30e
Source dataset
uspto-grants-1978_11
Patent number
US04126687

Reaction notes

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