Triethylamine → Oxime-2,3-dihydro-6-methoxy-1H-inden-1-one

HRID 577470Notes

Reaction equation

HRID 577470 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][C:9]2=O)=[CH:5][CH:4]=1.CCN(CC)CC.[NH2:20][OH:21].Cl>CO>[OH:21]/[N:20]=[C:9]1\[CH2:8][CH2:7][C:6]2[C:10]\1=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3340366-Methoxy-1-IndanoneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 11389720Oxime-2,3-dihydro-6-methoxy-1H-inden-1-oneYield 103.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred suspension of 6-methoxy-2,3-dihydro-1H-inden-1-one (15.0 g, 93.0 mmol) and Et3N (28.2 g, 279 mmol) in MeOH (200 mL) was added NH2OH.HCl (12.8 g, 186 mmol) at room temperature. After the addition, the resulting solution was stirred at room temperature for 24 hours. The reaction mixture was concentrated under vacuum. To the residue was added EtOAc (300 mL). The solution was washed with water (2×150 mL), brine (150 mL), dried over Na2SO4, and concentrated under vacuum to give (1E)-N-hydroxy-6-methoxy-2,3-dihydro-1H-inden-1-imine (1a, 17 g, >100%) as a white solid.

Workup

  1. additionAfter the addition
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. additionTo the residue was added EtOAc (300 mL)
  4. washThe solution was washed with water (2×150 mL), brine (150 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-221cb89194ec415ebf97b95dabe3f827
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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