m-Chloroperbenzoic acid → 5,6,7,8-tetrahydro 4-methylquinoline-N-oxide

HRID 1613579Notes

Reaction equation

HRID 1613579 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH3:12][C:13]1[C:22]2[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=2[N:16]=[CH:15][CH:14]=1>ClCCl>[CH3:12][C:13]1[C:22]2[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=2[N+:16]([O-:6])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 1856675,6,7,8-Tetrahydro-4-methylquinoline

Product 1

HCID 148359455,6,7,8-tetrahydro 4-methylquinoline-N-oxideYield 79.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred suspension of 3-chloroperoxybenzoic acid (34 g, 197 mmol) in dichloromethane (170 ml) at 0° was treated dropwise with 5,6,7,8-tetrahydro-4-methylquinoline (23.7 g, 161 mmol) in dichloromethane (30 ml), warmed to room temperature, washed with 1N-NaOH (3×200 ml), and extracted with dichloromethane (5×150 ml). The extracts were dried (MgSO4) and evaporated in vacuo to give the product (21 g) as an oil.

Workup

  1. washwashed with 1N-NaOH (3×200 ml)
  2. extractionextracted with dichloromethane (5×150 ml)
  3. dry with materialThe extracts were dried (MgSO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-134e73b687624b44adee84cb5efe030c
Source dataset
uspto-grants-1993_03
Patent number
US05194439

Reaction notes

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