Ammonia → 8-hydroxy-2-(4-nitrophenyl)-3H-quinazolin-4-one

HRID 850059Notes

Reaction equation

HRID 850059 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]3[C:13](=[C:15]([C:19]([O:21]C)=O)[CH:16]=[CH:17][CH:18]=3)[N:14]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH3:23]>>[OH:11][C:12]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:13]=1[N:14]=[C:10]([C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[NH:23][C:19]2=[O:21]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 14616766HCID 14616766, compound

Product 1

HCID 1354923898-hydroxy-2-(4-nitrophenyl)-3H-quinazolin-4-one

Procedure

Methyl 2-(4-nitrophenyl)benzoxazole-4-carboxylate (0.20 g) obtained as described in Example 19 (2nd stage) was dissolved in liquid ammonia (30 ml) and sealed in an autoclave. The reaction mixture was left at 55° C., 20 bar for 20 hours. Under these conditions, the expected 2-(4-nitrophenyl)benzoxazole derivative apparently rearranged to give the corresponding quinazolinone derivative. Once the reaction was complete the ammonia was removed and the resulting solid recrystallised from boiling ethyl acetate and petrol (84%).

Workup

  1. customsealed in an autoclave
  2. waitThe reaction mixture was left at 55° C.

Sources & evidence

ORD record
ord-0e282f509fdd4c8b9899cead3e380b30
Source dataset
uspto-grants-2000_01
Patent number
US06015827

Reaction notes

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