Hydroxyamine hydrochloride → 4-[3-(2-Amino-4-phenyl-quinolin-7-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile

HRID 2075664Notes

Reaction equation

HRID 2075664 reaction equation
C(=[N:14][C:15]1[CH:24]=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22]2[C:17](=[CH:18][C:19]([S:31][C:32]3[CH:33]=[C:34]([C:38]4([C:44]#[N:45])[CH2:43][CH2:42][O:41][CH2:40][CH2:39]4)[CH:35]=[CH:36][CH:37]=3)=[CH:20][CH:21]=2)[N:16]=1)(C1C=CC=CC=1)C1C=CC=CC=1.Cl.NO.C([O-])(=O)C.[K+]>CO>[NH2:14][C:15]1[CH:24]=[C:23]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:22]2[C:17](=[CH:18][C:19]([S:31][C:32]3[CH:33]=[C:34]([C:38]4([C:44]#[N:45])[CH2:39][CH2:40][O:41][CH2:42][CH2:43]4)[CH:35]=[CH:36][CH:37]=3)=[CH:20][CH:21]=2)[N:16]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517044Potassium AcetateHCID 866138274-{3-[2-(Benzhydrylidene-amino)-4-phenyl-quinolin-7-ylsulfanyl]-phenyl}-tetrahydro-pyran-4-carbonitrile

Product 1

HCID 670910914-[3-(2-Amino-4-phenyl-quinolin-7-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1s (110 mg, 0.18 mmol), hydroxylamine hydrochloride (25 mg, 0.36 mmol), and potassium acetate (44 mg, 0.45 mmol) were dissolved in MeOH (10 mL) and stirred at room temperature for 30 minutes. The reaction was concentrated and diluted with EtOAc and water. The aqueous layer was extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered, and concentrated to give 1t.

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with EtOAc and water
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialthe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6326624228f1468b82dae49d1326d9be
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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