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Dichloromethane → 4-(3-Hydroxy-4-methylanilino)-6-methoxy-7-(4-pyridylmethoxy)quinazoline hydrochloride

HRID 1384512
Notes
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Reaction equation

HRID 1384512 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]([CH:29]=[CH:30][C:31]=1[CH3:32])[NH:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)=[C:16]([O:19][CH3:20])[CH:17]=2)[N:12]=[CH:11][N:10]=1)(=O)C.[OH-].[Na+].C(Cl)[Cl:36]>CO>[ClH:36].[OH:4][C:5]1[CH:6]=[C:7]([CH:29]=[CH:30][C:31]=1[CH3:32])[NH:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)=[C:16]([O:19][CH3:20])[CH:17]=2)[N:12]=[CH:11][N:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 110373874-(3-Acetoxy-4-methylanilino)-6-methoxy-7-(4-pyridylmethoxy)quinazoline

Product 1

HCID 226249114-(3-Hydroxy-4-methylanilino)-6-methoxy-7-(4-pyridylmethoxy)quinazoline hydrochlorideYield 87%

Reagents, catalysts & solvents 1

HCID 887Methanol
Solvent

Procedure

To a solution of 4-(3-acetoxy-4-methylanilino)-6-methoxy-7-(4-pyridylmethoxy)quinazoline (93 mg, 0.2 mmol) in a mixture of methanol (6 ml) and methylene chloride (3 ml) was added at ambient temperature a 2M aqueous sodium hydroxide solution (0.3 ml, 0.6 mmol). The mixture was stirred for 10 minutes at ambient temperature, the solvents were partially evaporated, water was added to the residue and the solution was acidified with 0.1M hydrochloric acid to pH6. The precipitate was filtered off, washed with water and dried under vacuum to give 4-(3-hydroxy-4-methylanilino)-6-methoxy-7-(4-pyridylmethoxy)quinazoline hydrochloride (67 mg, 87%). m.p. 249-251° C. 1H NMR Spectrum: (DMSOd6) 2.13(s, 3H); 4.01(s, 3H); 5.40(s, 2H); 7.05(br s, 2H); 7.24(s, 1H); 7.34(s, 1H); 7.51(d, 2H); 7.92(s, 1H); 8.44(s, 1H); 8.63(d, 2H); 9.34(s, 1H); 9.47(br s, 1H) MS−ESI: 389 [MH]+

Workup

  1. customthe solvents were partially evaporated
  2. additionwater was added to the residue
  3. filtrationThe precipitate was filtered off
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-e91829582cab4e948cc9855a5c14fd5d
Source dataset
uspto-grants-2001_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06258951B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes