Water → (NZ)-N-[(4S)-4-(3,4-dichlorophenyl)-2-methyl-3,4-dihydro-2H-naphthalen-1-ylidene]hydroxylamine

HRID 556172Notes

Reaction equation

HRID 556172 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)[CH:11]([CH3:20])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[NH2:21][OH:22].Cl.CCN(CC)CC.O>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:21]\[OH:22])/[CH:11]([CH3:20])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 58950780(4S)-4-(3,4-dichlorophenyl)-2-methyl-3,4-dihydronaphthalen-1(2H)-one

Product 1

HCID 87161945(NZ)-N-[(4S)-4-(3,4-dichlorophenyl)-2-methyl-3,4-dihydro-2H-naphthalen-1-ylidene]hydroxylamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (4S)-4-(3,4-dichlorophenyl)-2-methyl-3,4-dihydronaphthalen-1(2H)-one (55) (1.2 g, 3.92 mmol) in CH2Cl2 (30 mL) and MeOH (20 mL) was added NH2OH.HCl (0.41 g, 5.92 mmol) and Et3N (1.19 g, 11.84 mmol). The reaction mixture was heated at reflux. After 1 h, H2O (10 mL0 was added and the resultant mixture was heated at reflux for 5 h before being concentrated. The residue was purified by silica gel column chromatography (ethyl acetatelhexane=1:7 to 1:5). Oxime 57, eluted from the column first (0.51 g, 41%) followed by the oxime 58 (0.49, 39%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux
  3. temperatureat reflux for 5 h
  4. concentrationbefore being concentrated
  5. customThe residue was purified by silica gel column chromatography (ethyl acetatelhexane=1:7 to 1:5)
  6. washOxime 57, eluted from the column first (0.51 g, 41%)

Sources & evidence

ORD record
ord-ca50ab971a3a40a79e9d616ec070ab7c
Source dataset
uspto-grants-2011_11
Patent number
US08053603B2

Reaction notes

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