Hydroxylamine → HCID 178486715, compound

HRID 2199676Notes

Reaction equation

HRID 2199676 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:22][CH2:23][C:24]#[N:25])=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[NH2:26][OH:27]>CCO>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:22][CH2:23][C:24](=[NH:25])[NH:26][OH:27])=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 66838691{[4-[(3,4-Dichlorophenyl)amino]-6-(methyloxy)quinazolin-7-yl]oxy}acetonitrile

Product 1

HCID 178486715HCID 178486715, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of {[4-[(3,4-dichlorophenyl)amino]-6-(methyloxy)quinazolin-7-yl]oxy}acetonitrile (14.7 g; 39.3 mmol) in EtOH (600 ml) was added a 50% aqueous solution of NH2OH (24.1 ml; 393 mmol) and the reaction mixture was refluxed for 2 hours. The solvent was evaporated off and the residue was triturated with ether, collected by filtration and dried under vacuum to give 2-{[4-[(3,4-dichlorophenyl)amino]-6-(methyloxy)quinazolin-7-yl]oxy}-N-hydroxyethanimidamide (14.5 g; 90% yield). 1H NMR (400 MHz; DMSO-d6): 3.98 (s, 3H), 4.58 (s, 2H), 5.70 (s, 2H), 7.38 (s, 1H), 7.65 (d, 1H), 7.84 (s, 1H), 7.89 (dd, 1H), 8.26 (d, 1H), 8.55 (s, 1H), 9.41 (s, 1H), 9.64 (s, 1H); MS (EI) for C17H15Cl2N5O3: 408.05 (MH+).

Workup

  1. temperaturethe reaction mixture was refluxed for 2 hours
  2. customThe solvent was evaporated off
  3. customthe residue was triturated with ether
  4. filtrationcollected by filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-6fd0795d397d441688f2c4a47f00a5f9
Source dataset
uspto-grants-2016_06
Patent number
US09359332B2

Reaction notes

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