Sodium Hydroxide → 7-(4-Fluoro-phenyl)-4-methoxy-benzooxazol-2-ylamine

HRID 1611949Notes

Reaction equation

HRID 1611949 reaction equation
COC(=O)[NH:4][C:5]1[O:6][C:7]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[CH:12][CH:11]=[C:10]([O:21][CH3:22])[C:8]=2[N:9]=1.[OH-].[Na+]>O1CCOCC1.C(O)CO>[F:20][C:17]1[CH:16]=[CH:15][C:14]([C:13]2[C:7]3[O:6][C:5]([NH2:4])=[N:9][C:8]=3[C:10]([O:21][CH3:22])=[CH:11][CH:12]=2)=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69288206[7-(4-Fluoro-phenyl)-4-methoxy-benzooxazol-2-yl]-carbamic acid methyl ester

Product 1

HCID 222522347-(4-Fluoro-phenyl)-4-methoxy-benzooxazol-2-ylamineYield 42%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 2.80 g (8.85 mmol) [7-(4-fluoro-phenyl)-4-methoxy-benzooxazol-2-yl]-carbamic acid methyl ester in 100 ml dioxane and 30 ml ethylene glycol was added 100 ml of a 5 N aq. sodium hydroxide solution, and the mixture was heated at 100° C. for 16 h. After cooling to room temperature the mixture was poured onto water and extracted three times with ethyl acetate. The combined organic phases were washed with brine, then dried over sodium sulphate and concentrated in vacuo. Trituration in ether afforded 0.95 g (42%) 7-(4-fluoro-phenyl)-4-methoxy-benzooxazol-2-yl-amine as an off-white solid. ES-MS m/e (%): 259 (M+H+, 100).

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. additionwas poured onto water
  3. extractionextracted three times with ethyl acetate
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-72ab26b5f9094ee893488c82fac68f44
Source dataset
uspto-grants-2006_01
Patent number
US06992083B2

Reaction notes

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