Hydrazine hydrate (1:1) → 3-Amino-6-chloro-4-phenyl-3,4-dihydroquinazolin-4-ol

HRID 2082690Notes

Reaction equation

HRID 2082690 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:16][CH:17]=O)=[C:6]([CH:15]=1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8].O.[NH2:20][NH2:21]>C(O)C>[NH2:20][N:21]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

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 82576N-(2-Benzoyl-4-chlorophenyl)formamide

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2.7 parts of 5-chloro-2-formamidobenzophenone in 40 volume parts of ethanol is added 2.5 volume parts of hydrazine hydrate, followed by refluxing for 20 minutes. After cooling, the resulting crystals are recovered by filtration and washed with ethanol and ether and then dried. This procedure gives 3-amino-6-chloro-3,4-dihydro-4-hydroxy-4-phenylquinazoline as crystals melting at 189° to 192° C. Yield: 95%.

Workup

  1. temperatureby refluxing for 20 minutes
  2. temperatureAfter cooling
  3. filtrationthe resulting crystals are recovered by filtration
  4. washwashed with ethanol and ether
  5. customdried

Sources & evidence

ORD record
ord-069c865c2f8e43c4b6f822612c27cbf7
Source dataset
uspto-grants-1978_04
Patent number
US04082764

Reaction notes

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