Ammonia → HCID 5329013, compound

HRID 634653Notes

Reaction equation

HRID 634653 reaction equation
N.C([O:5][C:6]1[C:7]([Cl:31])=[CH:8][C:9]([F:30])=[C:10]([CH:29]=1)[NH:11][C:12]1[C:21]2[C:16](=[CH:17][C:18]([O:24][CH2:25][CH2:26][O:27][CH3:28])=[C:19]([O:22][CH3:23])[CH:20]=2)[N:15]=[CH:14][N:13]=1)(=O)C>CO.O>[Cl:31][C:7]1[C:6]([OH:5])=[CH:29][C:10]([NH:11][C:12]2[C:21]3[C:16](=[CH:17][C:18]([O:24][CH2:25][CH2:26][O:27][CH3:28])=[C:19]([O:22][CH3:23])[CH:20]=3)[N:15]=[CH:14][N:13]=2)=[C:9]([F:30])[CH:8]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 21260358HCID 21260358, compound

Product 1

HCID 5329013HCID 5329013, compoundYield 46.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Concentrated aqueous ammonia (5 ml) was added to a solution of 4-(5-acetoxy-4-chloro-2-fluoroanilino)-6-methoxy-7-(2-methoxyethoxy)quinazoline (180 mg, 0.4 mmol) in methanol (50 ml). The mixture was stirred at ambient temperature for 3 hours, and then diluted with water. Most of the methanol was removed by evaporation and the resulting precipitate collected by filtration, washed with water and dried to give 4-(4-chloro-2-fluoro-5-hydroxyanilino)-6-methoxy-7-(2-methoxyethoxy)quinazoline (73 mg, 45%).

Workup

  1. customMost of the methanol was removed by evaporation
  2. filtrationthe resulting precipitate collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-a9be5bf9694d43858bf2068677993cdc
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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