Dichloromethane → Ethyl 2-(hydroxyamino)benzoate

HRID 1054211Notes

Reaction equation

HRID 1054211 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].[Cl-].[NH4+].C1COCC1.C(Cl)Cl>O.[Zn]>[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

7

Reactant 4

HCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 69123Ethyl 2-nitrobenzoate

Product 1

HCID 13571167Ethyl 2-(hydroxyamino)benzoateYield 50%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent2×

Procedure

To a stirring solution of ethyl 2-nitrobenzoate (32.0 g, 0.164 mol), ammonium chloride (22.28 g, 0.416 mol) in solvent mixture of water (240 mL) and THF (288 mL) was added zinc powder (26.8 g, 0.410 mol) slowly at 0° C. Reaction mixture was stirred at 0° C.-10° C. for 2 h. Reaction mixture was then diluted with water followed by DCM and filtered through Hyflow bed. The organic layer was separated and distilled out to get crude product which was column purified using 0-5% EtOAC in hexane to get titled compound as light yellow solid in 50% yield.

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. filtrationfiltered through Hyflow bed
  4. customThe organic layer was separated
  5. distillationdistilled out
  6. customto get crude product which
  7. custompurified

Sources & evidence

ORD record
ord-88ffe8077b65421a982177dd3edef6a5
Source dataset
uspto-grants-2016_07
Patent number
US09394300B2

Reaction notes

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