Diethyl Ether → Methyl 2-amino-6-chloro-4-trifluoromethylbenzoate

HRID 3131

Reaction equation

HRID 3131 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[C:9]2[C:10](=[O:15])[O:11][C:12](=O)[NH:13][C:8]=2[CH:7]=[C:6]([C:16]([F:19])([F:18])[F:17])[CH:5]=1.C(OCC)C>CO>[NH2:13][C:8]1[CH:7]=[C:6]([C:16]([F:17])([F:18])[F:19])[CH:5]=[C:4]([Cl:3])[C:9]=1[C:10]([O:11][CH3:12])=[O:15]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 189299275-Chloro-7-trifluoromethyl-2H-3,1-benzoxazine-2,4(1H)-dione

Product 1

HCID 18929885Methyl 2-amino-6-chloro-4-trifluoromethylbenzoateYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of sodium hydroxide (0.012 g, 0.31 mM) in anhydrous methanol (1.5 mL) under a nitrogen atmosphere was added 5-chloro-7-trifluoromethyl-2H-3,1-benzoxazine-2,4(1H)-dione (0.60 g, 2.3 mM). The resulting mixture was warmed to 60° C. for 0.5 hr, allowed to cool to room temperature and poured into diethyl ether. The ether was washed with water, dried (MgSO4), filtered and concentrated to leave (0.50 g, 88%) the title compound as a yellow oil; MS(CI): 254 (M+H).

Workup

  1. temperatureto cool to room temperature
  2. washThe ether was washed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-de691adb4df542928566b3b06e2c218d
Source dataset
uspto-grants-1998_03
Patent number
US05733910

Linked notes

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