Borane;tetrahydrofuran → HCID 89923979, compound

HRID 1500906Notes

Reaction equation

HRID 1500906 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([NH:11][C:12](=O)[CH2:13][C:14]([F:17])([F:16])[F:15])=[C:4]([F:19])[CH:3]=1.B.O1CCCC1>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([NH:11][CH2:12][CH2:13][C:14]([F:15])([F:16])[F:17])=[C:4]([F:19])[CH:3]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 89923780HCID 89923780, compound

Product 1

HCID 89923979HCID 89923979, compoundYield 106.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of N-(4-chloro-2-fluoro-6-nitrophenyl)-3,3,3-trifluoropropanamide (350 mg, 1.1 mmol) in 15 mL of THF was added borane-tetrahydrofuran solution (25 mL, 1 M). The mixture was heated to 70° C. and stirred overnight. The reaction was quenched with MeOH and the solvents were removed by evaporation to give 4-chloro-6-fluoro-N-(3,3,3-trifluoropropyl)benzene-1,2-diamine (300 mg, yield: 82%) as crude oil. MS obsd. (ESI+) [(M+H)+] 257.

Workup

  1. customThe reaction was quenched with MeOH
  2. customthe solvents were removed by evaporation

Sources & evidence

ORD record
ord-b83c6805c78d4dbea8eb488945aa635a
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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