3-Chloro-4-(3-fluorobenzyloxy)aniline → 6-Bromo-N-{3-chloro-4-[(3-fluorophenyl)methoxy]phenyl}quinazolin-4-amine

HRID 1875493Notes

Reaction equation

HRID 1875493 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2Cl.[Cl:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][C:20]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=1)[NH2:17]>C(O)(C)C>[Cl:13][C:14]1[CH:15]=[C:16]([NH:17][C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([Br:1])[CH:3]=3)[N:8]=[CH:7][N:6]=2)[CH:18]=[CH:19][C:20]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=1

Participants

4

Reactant 2

HCID 70592633-Chloro-4-(3-fluorobenzyloxy)anilineHCID 167703106-Bromo-4-chloro-quinazoline

Product 1

HCID 247378566-Bromo-N-{3-chloro-4-[(3-fluorophenyl)methoxy]phenyl}quinazolin-4-amineYield 86%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

6-bromo-4-chloro-quinazoline (1.36 g) and 3-chloro-4(m-fluoro-benzyloxy)-aniline (1.42 g) were dissolved into 50 mL of isopropanol. The mixture was reacted under reflux for 3 h, and a lot of yellow solid was deposited. The precipitated solid was filtered, and the filter cake was washed with cold ethanol and dried at 60° C. under vacuum overnight to obtain the 6-bromo-4-aminoquinazoline product (2.20 g, 86%).

Workup

  1. customThe mixture was reacted
  2. temperatureunder reflux for 3 h
  3. filtrationThe precipitated solid was filtered
  4. washthe filter cake was washed with cold ethanol
  5. customdried at 60° C. under vacuum overnight

Sources & evidence

ORD record
ord-a3a066f3f6b84220bd4cb6d7e01acfb5
Source dataset
uspto-grants-2012_11
Patent number
US08309563B2

Reaction notes

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