Hydrochloric Acid → 4-(3-Ethynylphenylamino)-7-methoxyquinazolin-6-ol

HRID 712405Notes

Reaction equation

HRID 712405 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[CH:10][N:9]=[C:8]2[NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[CH:25])[CH:19]=1)(=O)C.[OH-].[Na+].Cl>CO>[C:24]([C:20]1[CH:19]=[C:18]([NH:17][C:8]2[C:7]3[C:12](=[CH:13][C:14]([O:15][CH3:16])=[C:5]([OH:4])[CH:6]=3)[N:11]=[CH:10][N:9]=2)[CH:23]=[CH:22][CH:21]=1)#[CH:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 219252474-((3-Ethynylphenyl)amino)-7-methoxyquinazolin-6-yl acetate

Product 1

HCID 219252124-(3-Ethynylphenylamino)-7-methoxyquinazolin-6-olYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 4-((3-ethynylphenyl)amino)-7-methoxyquinazolin-6-yl acetate (4.54 g) and methanol (30 mL) was added 5 mol/L NaOH (10.00 mL) at room temperature. The reaction mixture was stirred at room temperature for 5 h, and was adjusted to pH 7 with 0.1 N HCl (aq). The mixture was filtered to give the title compound as a white solid (3.30 g, 86.00%).

Workup

  1. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-b455bd7b5f0748aa91a9c8b281cc5d18
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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