Water → (NZ)-N-[(4S)-4-(3,4-dichlorophenyl)-2,2-dimethyl-3,4-dihydronaphthalen-1-ylidene]hydroxylamine

HRID 556173Notes

Reaction equation

HRID 556173 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=O)[C:11]([CH3:21])([CH3:20])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[OH2:22].[NH2:23]O.Cl.CCN(CC)CC>C(Cl)Cl.CO>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)/[C:12](=[N:23]\[OH:22])/[C:11]([CH3:21])([CH3:20])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 66809033(S)-4-(3,4-dichlorophenyl)-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one

Product 1

HCID 58950732(NZ)-N-[(4S)-4-(3,4-dichlorophenyl)-2,2-dimethyl-3,4-dihydronaphthalen-1-ylidene]hydroxylamineYield 84%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-4-(3,4-dichlorophenyl)-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one (56) (0.8 g, 2.51 mmol) in CH2Cl2 (20 mL) and MeOH (15 mL)-H2O (5 mL) was added NH2OH.HCl (0.35 g, 5.04 mmol) and Et3N (1.01 g, 10.1 mmol). The resultant mixture was heated at reflux for 5 h before being concentrated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1:7 to 1:5) to give (S,Z)-4-(3,4-dichlorophenyl)-2,2-dimethyl-3,4-dihydronaphthalen-1 (2H)-one oxime (60) (0.72 g, 84%).

Workup

  1. temperatureat reflux for 5 h
  2. concentrationbefore being concentrated
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1:7 to 1:5)

Sources & evidence

ORD record
ord-2f0d3c7cc10944828b198dbfc1e3b65c
Source dataset
uspto-grants-2011_11
Patent number
US08053603B2

Reaction notes

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