Hydroxyamine hydrochloride → 1-(2,6-Dichlorophenyl)-5-(2-chlorophenyl)-7-(1-hydroxyiminocyclohexan-4-yl)-3,4-dihydro-2(1H)-quinazolinone

HRID 394090Notes

Reaction equation

HRID 394090 reaction equation
Cl.[NH2:2][OH:3].[C:4]([O-:7])(O)=O.[Na+].[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:11]=1[N:17]1[C:26]2[C:21](=[C:22]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[Cl:40])[CH:23]=[C:24]([CH:27]3[CH2:32][CH2:31][C:30](=O)[CH2:29][CH2:28]3)[CH:25]=2)[CH2:20][NH:19]C1=O>CO>[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:11]=1[N:17]1[C:26]2[C:21](=[C:22]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[Cl:40])[CH:23]=[C:24]([CH:27]3[CH2:32][CH2:31][C:30](=[N:2][OH:3])[CH2:29][CH2:28]3)[CH:25]=2)[CH2:20][NH:19][C:4]1=[O:7]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 226480091-(2,6-Dichlorophenyl)-5-(2-chlorophenyl)-7-(1-cyclohexanon-4-yl)-3,4-dihydro-2(1H)-quinazolinone2×

Product 1

HCID 226481531-(2,6-Dichlorophenyl)-5-(2-chlorophenyl)-7-(1-hydroxyiminocyclohexan-4-yl)-3,4-dihydro-2(1H)-quinazolinone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of hydroxylamine hydrochloride (29 mg, 0.416 mmol) in methanol (1.0 mL) was added solid NaHCO3 (37 mg, 0.437 mmol). After stirring 15 minutes at RT 1-(2,6-Dichlorophenyl)-5-(2-chlorophenyl)-7-(1-cyclohexanon-4-yl)-3,4-dihydro-2(1H)-quinazolinone (52 mg, 0.104 mmol) (INTERMEDIATE 73) was added. After stirring 18 hours the solution was concentrated. The residue was suspended in DCM and the solid filtered. The filtrate solution was concentrated and the residue purified by preparative thin layer chromatography using 5% MeOH in DCM as the eluent to give 1-(2,6-Dichlorophenyl)-5-(2-chlorophenyl)-7-(1-hydroxyiminocyclohexan-4-yl)-3,4-dihydro-2(1H)-quinazolinone. 1H NMR (CDCl3, 500 MHz): selected data 1.53 (m, 2H), 1.87 (dt, 1H, J=5.4, 14.2 Hz), 1.98 (m, 2H), 2.19 (m, 1H), 2.57 (brd, 1H, J=14.4 Hz), 2.64 (m, 1H), 3.38 (brd, 1H, J=15.2 Hz).

Workup

  1. additionwas added
  2. concentrationwas concentrated
  3. filtrationthe solid filtered
  4. concentrationThe filtrate solution was concentrated
  5. customthe residue purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-70e333731d734a9d97b4dda8c4631195
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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