Water → HCID 21220385, compound

HRID 1584807Notes

Reaction equation

HRID 1584807 reaction equation
[N:1]([C:4]1[C:14]([F:15])=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([F:16])[C:5]=1[CH3:17])=[N+]=[N-].C(OCC)C.O.[OH-].[Na+]>CO>[NH2:1][C:4]1[C:14]([F:15])=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([F:16])[C:5]=1[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 21220291HCID 21220291, compound

Product 1

HCID 21220385HCID 21220385, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

In 60 ml of methanol was suspended 14.2 g of stannous chloride, and to this suspension was dropwise added a solution of 10.0 g of ethyl 4-azido-2,5-difluoro-3-methylbenzoate in 20 ml of methanol at room temperature over one hour, after which the resulting mixture was stirred at the same temperature for 30 minutes. The methanol was removed by distillation under reduced pressure, and to the residue obtained were added 300 ml of diethyl ether and 100 ml of water, after which the pH was adjusted to 12.5 with 2N aqueous sodium hydroxide solution. The organic layer formed was separated, washed with water and then dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure to obtain 8.91 g of yellow, oily ethyl 4-amino-2,5-difluoro-3-methylbenzoate.

Workup

  1. customThe methanol was removed by distillation under reduced pressure
  2. customto the residue obtained
  3. customThe organic layer formed
  4. customwas separated
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was then removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-b41cb406e22d4d95ab1fe3bd6484bcf6
Source dataset
uspto-grants-1999_08
Patent number
US05935952

Reaction notes

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