Water → tert-Butyl 2-amino-5-methylbenzoate

HRID 42001Notes

Reaction equation

HRID 42001 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:15]C(=O)C(F)(F)F)=[C:6]([CH:14]=1)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[BH4-].[Na+].O>C(O)C>[NH2:15][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:14][C:6]=1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 19261480HCID 19261480, compound

Product 1

HCID 13399998tert-Butyl 2-amino-5-methylbenzoateYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of tert-butyl 5-methyl-2-(2,2,2-trifluoroacetamido)benzoate (19.78 mmol, 6.0 g) in ethanol (19 ml) was cooled with a water-iced bath. NaBH4 (39.57 mmol, 1.50 g) was added in portions and the mixture was stirred at room temperature for 3 hours. Water (40 ml) was added slowly and evaporated. The solid was dissolved with CHCl3 and washed with water and brine. The organic phase was evaporated affording 3.73 g (yield 91%) of the expected product.

Workup

  1. temperaturewas cooled with a water-iced bath
  2. customevaporated
  3. dissolutionThe solid was dissolved with CHCl3
  4. washwashed with water and brine
  5. customThe organic phase was evaporated

Sources & evidence

ORD record
ord-39172d33d0c54e08af4d16110d3dbcd4
Source dataset
uspto-grants-2013_09
Patent number
US08536165B2

Reaction notes

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