Trifluoroacetic acid → 3-(2-Chloro-6,7-dimethoxyquinazolin-4-yl)phenylamine

HRID 453663Notes

Reaction equation

HRID 453663 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]([C:12]2[CH:13]=[C:14]([NH:18]C(=O)OC(C)(C)C)[CH:15]=[CH:16][CH:17]=2)[C:9]2[C:4](=[CH:5][C:6]([O:28][CH3:29])=[C:7]([O:26][CH3:27])[CH:8]=2)[N:3]=1.FC(F)(F)C(O)=O.[OH-].[Na+]>>[Cl:1][C:2]1[N:11]=[C:10]([C:12]2[CH:13]=[C:14]([NH2:18])[CH:15]=[CH:16][CH:17]=2)[C:9]2[C:4](=[CH:5][C:6]([O:28][CH3:29])=[C:7]([O:26][CH3:27])[CH:8]=2)[N:3]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 86650315t-Butyl [3-(2-chloro-6,7-dimethoxyquinazolin-4-yl)phenyl]carbamate

Product 1

HCID 576095393-(2-Chloro-6,7-dimethoxyquinazolin-4-yl)phenylamineYield 96.9%

Conditions

Temperature
5 °C

Procedure

Under a nitrogen atmosphere, 420 mg (1.00 mmol) of t-butyl [3-(2-chloro-6,7-dimethoxyquinazolin-4-yl)phenyl]carbamate was allowed to cool down to 5° C., trifluoroacetic acid (1 mL) was added dropwise while stirring, and the mixture was stirred at room temperature. The mixture was stirred for 1.25 hours, then allowed to cool down to 5° C. to 10° C., 2 N aqueous sodium hydroxide solution (6.2 mL) was added dropwise to precipitate pale yellow crystals. The mixture was stirred at room temperature for 15 minutes, and the precipitated crystals were filtration and dried to give 306 mg of a target product (yield: 95.6%).

Workup

  1. stirringthe mixture was stirred at room temperature
  2. stirringThe mixture was stirred for 1.25 hours
  3. temperatureto cool down to 5° C. to 10° C.
  4. customto precipitate pale yellow crystals
  5. stirringThe mixture was stirred at room temperature for 15 minutes
  6. filtrationfiltration
  7. customdried

Sources & evidence

ORD record
ord-12178f500fd24e23a820f90266539ab5
Source dataset
uspto-grants-2013_07
Patent number
US08492543B2

Reaction notes

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