Hydrochloric Acid → 4-(2-Fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-(4-pyridylmethoxy)quinazoline hydrochloride

HRID 1384528Notes

Reaction equation

HRID 1384528 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[F:22][C:23]1[CH:29]=[C:28]([CH3:30])[C:27]([OH:31])=[CH:26][C:24]=1[NH2:25].Cl>C(O)(C)C>[ClH:1].[F:22][C:23]1[CH:29]=[C:28]([CH3:30])[C:27]([OH:31])=[CH:26][C:24]=1[NH:25][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 101540985-Amino-4-fluoro-2-methylphenolHCID 226249154-Chloro-6-methoxy-7-(4-pyridylmethoxy)quinazoline

Product 1

HCID 226249294-(2-Fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-(4-pyridylmethoxy)quinazoline hydrochlorideYield 51.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A stirred solution of 4-chloro-6-methoxy-7-(4-pyridylmethoxy)quinazoline (35mg, 0.1 mmol) and 2-fluoro-5-hydroxy-4-methylaniline (15 mg, 0.1 mmol) in a mixture of ethereal hydrogen chloride (2 ml) and isopropanol (5 ml) was heated at reflux for 4 hours. The precipitated product was collected by filtration, washed with acetone and dried under vacuum to give 4-(2-fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-(4-pyridylmethoxy)quinazoline hydrochloride (23mg, 47%). m.p. 257-260° C. 1H NMR Spectrum: (DMSOd6) 2.15(s, 3H); 4.08(s, 3H); 5.60(s, 2H); 6.90(d, 1H); 7.07(d, 1H); 7.47(s, 1H); 7.93(br d, 2H); 8.74(s, 1H); 8.89(br d, 2H); 9.62(br s, 1H); 11.46(s, 1H) MS-ESI: 407 [MH]+

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. filtrationThe precipitated product was collected by filtration
  4. washwashed with acetone
  5. customdried under vacuum

Sources & evidence

ORD record
ord-d026296a7dde41018e50c7664643da41
Source dataset
uspto-grants-2001_07
Patent number
US06258951B1

Reaction notes

Loading…