Ethanol → 3-Amino-6-chloro-4-phenyl-3,4-dihydroquinazolin-4-ol

HRID 2082691Notes

Reaction equation

HRID 2082691 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:16]=[CH:17][N:18](C)C)=[C:6]([CH:15]=1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8].C(O)C.O.[NH2:25]N>C(O)(=O)C>[NH2:25][N:18]1[C:7]([OH:8])([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]2[C:5](=[CH:4][CH:3]=[C:2]([Cl:1])[CH:15]=2)[N:16]=[CH:17]1

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 203604375-Chloro-2-(((dimethylamino)methylene)amino)benzophenone

Product 1

HCID 1196793-Amino-6-chloro-4-phenyl-3,4-dihydroquinazolin-4-olYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 0.29 part of 5-chloro-2-dimethylaminomethyleneaminobenzophenone in 4 volume parts of ethanol are added 0.2 volume part of hydrazine hydrate and 0.06 volume part of glacial acetic acid. The mixture is shaken and kept standing at room temperature for about 30 minutes. The resulting crystals are recovered by filtration and washed with ethanol and then dried, whereby 3-amino-6-chloro-3,4-dihydro-4-hydroxy-4-phenylquinazoline is obtained as colorless needles melting at 185° (softening) to 192° C. This compound is identical with the product obtained in Example 1. Yield: 95%.

Workup

  1. filtrationThe resulting crystals are recovered by filtration
  2. washwashed with ethanol
  3. customdried

Sources & evidence

ORD record
ord-0d4feaeec8f64891a889f6fae85d059c
Source dataset
uspto-grants-1978_04
Patent number
US04082764

Reaction notes

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