Hydrochloric Acid → 4-(4-Chloro-2-fluoroanilino)-6-methoxyquinazoline

HRID 1838573Notes

Reaction equation

HRID 1838573 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([NH:6][C:7]2[C:16]3[C:11](=[CH:12][C:13](OCCCC(OCC)=O)=[C:14]([O:17][CH3:18])[CH:15]=3)[N:10]=[CH:9][N:8]=2)=[C:4]([F:30])[CH:3]=1.O.CO.Cl>[OH-].[Na+]>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([NH:6][C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=3)[N:10]=[CH:9][N:8]=2)=[C:4]([F:30])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 962WaterHCID 224783014-(4-Chloro2-fluoroanilino)-7-(3-ethoxycarbonylpropoxy)6-methoxyquinazoline

Product 1

HCID 865864644-(4-Chloro-2-fluoroanilino)-6-methoxyquinazolineYield 111.9%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 4-(4chloro-2-fluoroanilino)-7-(3-ethoxycarbonylpropoxy)-6-methoxyquinazoline (220 mg, 0.5 mmol) in aqueous sodium hydroxide solution (4 ml of a 2M solution, 8 mmol), water (2 ml) and methanol (0.5 ml) was stirred and heated at 40° C. for 3 hours. The mixture was allowed to cool and was then acidified with 2M hydrochloric acid. The resulting white precipitate was collected by filtration and washed with acetone and water to give 7-3-carboxypropoxy)-4-(4-chloro-2-fluoroanilino)-6-methoxyquinazoline (170 mg, 83%).

Workup

  1. temperatureto cool
  2. filtrationThe resulting white precipitate was collected by filtration
  3. washwashed with acetone and water

Sources & evidence

ORD record
ord-f3aab247b3b94388a459d220825694cf
Source dataset
uspto-grants-2004_01
Patent number
US06673803B2

Reaction notes

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