4-Amino-1-butanol → HCID 23295819, compound

HRID 1954025Notes

Reaction equation

HRID 1954025 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][OH:6].F[C:8]1[CH:13]=[C:12]([F:14])[C:11]([C:15]([F:18])([F:17])[F:16])=[CH:10][C:9]=1[N+:19]([O-:21])=[O:20]>C(O)C>[F:14][C:12]1[C:11]([C:15]([F:16])([F:17])[F:18])=[CH:10][C:9]([N+:19]([O-:21])=[O:20])=[C:8]([CH:13]=1)[NH:1][CH2:2][CH2:3][CH2:4][CH2:5][OH:6]

Participants

4

Reactant 2

HCID 258684-Amino-1-butanolHCID 232958112,4-Difluoro-5-nitrobenzotrifluoride

Product 1

HCID 23295819HCID 23295819, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

With ice-cooling, 4-aminobutanol (0.72 g) dissolved in ethanol (5 ml) was added dropwise to ethanol (10 ml) solution of 1,5-difluoro-2-nitro-4-trifluoromethylbenzene (0.73 g), and the reaction was carried out overnight at room temperature. The reaction solution was concentrated and the resulting residue was purified by a silica gel column chromatography (n-hexane:ethyl acetate=1:1) to give 4-(5-fluoro-2-nitro-4-trifluoromethylanilino)butanol (0.76 g). The resulting anilinobutanol (0.66 g) and imidazole (1.5 g) were allowed to react with each other in DMF (10 ml) at 140° C. for 1 hour, the reaction solution was concentrated and then the resulting residue was purified by a silica gel column chromatography (chloroform:methanol =15:1) to give 4-[5-(1H-imidazol-1-yl)-2-nitro-4-trifluoromethylanilino)butanol (0.68 g).

Workup

  1. temperatureWith ice-cooling
  2. concentrationThe reaction solution was concentrated
  3. customthe resulting residue was purified by a silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-59ed3118f3e84e8e840e2955840cf53f
Source dataset
uspto-grants-2000_09
Patent number
US06121264

Reaction notes

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