Methanol → 4-Chloro-2-fluoro-5-(diisopropylaminomethyl)aniline

HRID 231438Notes

Reaction equation

HRID 231438 reaction equation
[CH:1]([N:4]([CH2:8][C:9]1[CH:14]=[C:13]([N:15](C(=O)C)C(=O)C)[C:12]([F:22])=[CH:11][C:10]=1[Cl:23])[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[OH-].[K+].CO.O>C(OCC)C>[Cl:23][C:10]1[C:9]([CH2:8][N:4]([CH:5]([CH3:7])[CH3:6])[CH:1]([CH3:2])[CH3:3])=[CH:14][C:13]([NH2:15])=[C:12]([F:22])[CH:11]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14797Potassium HydroxideHCID 20032363N,N-diisopropyl-2-chloro-4-fluoro-5-diacetylaminobenzylamine

Product 1

HCID 197395974-Chloro-2-fluoro-5-(diisopropylaminomethyl)anilineYield 92%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 0.72 g (0.0021 mole) of N,N-diiso-propyl-2-chloro-4-fluoro-5-diacetylaminobenzylamine, 1 g (0.018 mole) of potassium hydroxide, 20 ml of methanol, and 5 ml of water was refluxed for six hours. After cooling to room temperature, the reaction mixture was diluted with diethyl ether and was washed with water. The aqueous washes were combined and extracted with methylene chloride. These extracts were combined with the diethyl ether solution. This mixture was dried, filtered, and the solvents were evaporated under reduced pressure, yielding 0.50 g of 4-chloro-2-fluoro-5-(diisopropylaminomethyl)aniline. The nmr and ir spectra were consistent with the proposed structure.

Workup

  1. temperaturewas refluxed for six hours
  2. washwas washed with water
  3. extractionextracted with methylene chloride
  4. customThis mixture was dried
  5. filtrationfiltered
  6. customthe solvents were evaporated under reduced pressure

Sources & evidence

ORD record
ord-488974dc911f46ca9bf791062813d3a5
Source dataset
uspto-grants-1989_07
Patent number
US04846882

Reaction notes

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