4-Chloroaniline → HCID 21098398, compound
Reaction equation
[C:1]([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][NH:9][C:8]2=O)(=[O:3])[CH3:2].[Cl:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1>O=S(Cl)Cl.CN(C=O)C>[C:1]([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:23][C:22]1[CH:24]=[CH:25][C:19]([Cl:18])=[CH:20][CH:21]=1)(=[O:3])[CH3:2]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 6-acetoxy-7-methoxy-quinazolin-4-one (RO0505111-000) (1.0 g, 4.26 mmol) (from Example 15, Step A, supra) in SOCl2 (12.5 mL) (Aldrich) was added a few drops of DMF (0.1 mL). The reaction mixture was then heated with stirring at 100° C. for 3 hours. The solvents were evaporated and the residue was dried in vacuo. The residue was dissolved in 2-propanol (20 mL), then 4-chloroaniline (0.6 g, 4.69 mmol) (Fluka) was added. The reaction mixture was heated at 110° C. for 3 hours. The reaction mixture was cooled to room temperature and filtered. The precipitate was collected and dried in vacuo to give 6-acetoxy-4-(4-chloro-phenylamino)-7-methoxy-quinazoline as a gray solid. (Yield 1.45 g, 99%).
Workup
- temperatureThe reaction mixture was then heated
- customThe solvents were evaporated
- customthe residue was dried in vacuo
- dissolutionThe residue was dissolved in 2-propanol (20 mL)
- temperatureThe reaction mixture was heated at 110° C. for 3 hours
- temperatureThe reaction mixture was cooled to room temperature
- filtrationfiltered
- customThe precipitate was collected
- customdried in vacuo
Sources & evidence
- ORD record
- ord-4cd0afffd62641ea950ffa06de89923e
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07217717B2
Reaction notes
Loading…