2-Amino-3-methoxybenzamide → HCID 135471356, compound

HRID 1274071Notes

Reaction equation

HRID 1274071 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1)[NH:8][C:7]2=[O:21].COC1C(N)=C(C=CC=1)C(N)=O.[H][H]>CO.[C].[Pd]>[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=1)[NH:8][C:7]2=[O:21]

Participants

6

Reactant 3

HCID 185365712-Amino-3-methoxybenzamideHCID 1354923898-hydroxy-2-(4-nitrophenyl)-3H-quinazolin-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 135471356HCID 135471356, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent2×

Procedure

8-Hydroxy-2-(4'-nitrophenyl)quinazolin-4-[3 H]-one, prepared from 3-methoxy-2-aminobenzamide as in Example 5, (50 mg, 0.18 mmol) was suspended in methanol (20 ml) with palladium-carbon catalyst (20 mg) and the reaction vessel was placed under the atmosphere of hydrogen at ambient temperature and pressure. The reaction mixture changed from a yellow suspension to a clear, colourless solution, whereupon the catalyst was removed by filtration through Celite™. The solvent was removed under vacuum to leave a cream pale brown solid, which was recystallised from aq. methanol (25.7 mg, 0.1 mmol, 57%), m.p. >230° C.

Workup

  1. customwhereupon the catalyst was removed by filtration through Celite™
  2. customThe solvent was removed under vacuum
  3. customto leave a cream pale brown solid, which

Sources & evidence

ORD record
ord-b5d0445d9d5d4bbc9eef6286afa462be
Source dataset
uspto-grants-2000_12
Patent number
US06156739

Reaction notes

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