Methanol → Ethyl 2-(hydroxyamino)benzoate

HRID 1054217Notes

Reaction equation

HRID 1054217 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7])([O-])=[O:2].O.O.O.C([O-])(=O)C.[Na+].CO.C1COCC1>O.C(=O)(O)[O-].[Na+].CCCCCC>[OH:2][NH:1][C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

8

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 69123Ethyl 2-nitrobenzoateHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 13571167Ethyl 2-(hydroxyamino)benzoateYield 80%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8058HexaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
27.5 °C

Procedure

To a stirring solution of ethyl 2-nitrobenzoate (1.0 g, 5.12 mmol), sodium acetate trihydrate (4.18 g, 30.7 mmol) in solvent mixture of MeOH (7 ml) and THF (7 ml) was added stannous chloride dihydrate (3.47 g, 15.37 mmol) slowly at 10-20° C. Reaction mixture was stirred at 25-30° C. for 16 h. Reaction mixture was diluted with water and basified with aq. sodium bicarbonate solution. Product was extracted with ethyl acetate. The organic layer was separated and distilled out to get crude product which was stirred with hexane to get white solid in 80% yield.

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. extractionProduct was extracted with ethyl acetate
  4. customThe organic layer was separated
  5. distillationdistilled out
  6. customto get crude product which
  7. customto get white solid in 80% yield

Sources & evidence

ORD record
ord-f79c3eafdb934bca94dd1b7e9707d1d6
Source dataset
uspto-grants-2016_07
Patent number
US09394300B2

Reaction notes

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