Dimethylformamide → 4-Chloro-6-methoxyquinazolin-7-ol

HRID 2084009Notes

Reaction equation

HRID 2084009 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=O)[NH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])C1C=CC=CC=1.CN(C)C=O.S(Cl)([Cl:29])=O>>[Cl:29][C:13]1[C:12]2[C:17](=[CH:18][C:9]([OH:8])=[C:10]([O:20][CH3:21])[CH:11]=2)[N:16]=[CH:15][N:14]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 1354047187-Benzyloxy-6-methoxy-3H-quinazolin-4-one

Product 1

HCID 1357422514-Chloro-6-methoxyquinazolin-7-olYield 100%

Procedure

7-Benzyloxy-6-methoxy-3,4-dihydroquinazolin-4-one (10.1 g) was suspended in thionyl chloride (200 ml) then dimethylformamide (0.5 ml) added and the resultant mixture heated to 80° C. and stirred for 3 hours. The reaction mixture was evaporated and azeotroped with toluene to yield 4-chloro-7-hydroxy-6-methoxyquinazoline as a solid (12.1 g, 100%); NMR: 4.88 (s, 3H), 5.25 (s, 2H), 7.44 (s, 1H), 7.49 (s, 1H), 7.32-7.52 (m, 5H), 8.83 (s, 1H); m/s: M+H+ 283.

Workup

  1. customThe reaction mixture was evaporated
  2. customazeotroped with toluene

Sources & evidence

ORD record
ord-fbc10e81a59e44699f61d42ee732f32b
Source dataset
uspto-grants-2004_04
Patent number
US06716847B2

Reaction notes

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