Hydrochloric Acid → 6-(benzyloxy)-7-methoxy-2-(3-nitrophenyl)quinazolin-4(3H)-one

HRID 61644Notes

Reaction equation

HRID 61644 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][C:6]([C:7]([NH2:9])=[O:8])=[C:5]([NH:20][C:21](=O)[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-:30])=[O:29])[CH:23]=2)[CH:4]=1.N1C=CC=CC=1.Cl>[OH-].[Na+]>[CH2:13]([O:12][C:11]1[CH:10]=[C:6]2[C:5](=[CH:4][C:3]=1[O:2][CH3:1])[N:20]=[C:21]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-:30])=[O:29])[CH:23]=1)[NH:9][C:7]2=[O:8])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 1049PyridineHCID 59361865HCID 59361865, compound

Product 1

HCID 1362032466-(benzyloxy)-7-methoxy-2-(3-nitrophenyl)quinazolin-4(3H)-oneYield 47%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A suspension of 4-methoxy-5-benzyloxy-2-(3-nitrobenzoylamino) benzamide (8.00 g, possesses some pyridine.HCl) in 4N NaOH (200 mL) was heated at 100±5° C. for 10 h. The reaction mixture was allowed to cool to room temperature and pH was adjusted to 7-7.5 with 6 N HCl. A solid separated out, which was collected by filtration, washed with water (100 mL) and dried under vacuum to give 6-(benzyloxy)-7-methoxy-2-(3-nitrophenyl)quinazolin-4(3H)-one (3.22 g, 7.99 mmol, 47% over two steps). MS 404 (M+1) HPLC retention time 8.026 min.

Workup

  1. customA solid separated out
  2. filtrationwhich was collected by filtration
  3. washwashed with water (100 mL)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-d0d55d68c68e48a0af86bb241a26732d
Source dataset
uspto-grants-2016_09
Patent number
US09440961B2

Reaction notes

Loading…