N-ethyl-3-methylaniline → N-Ethyl-3-Hydroxy-7-Methyl-1,2,3,4-Tetrahydroquinoline

HRID 435072

Reaction equation

HRID 435072 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[CH:5]=1)[CH3:2].[CH2:11]([CH:13]1[O:15][CH2:14]1)Cl>>[CH2:1]([N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([CH3:10])[CH:5]=2)[CH2:14][CH:13]([OH:15])[CH2:11]1)[CH3:2]

Participants

3

Reactant 2

HCID 7603N-ethyl-3-methylanilineHCID 7835Epichlorohydrin

Product 1

HCID 20277626N-Ethyl-3-Hydroxy-7-Methyl-1,2,3,4-Tetrahydroquinoline

Procedure

N-ethyl-m-toluidine (1.0 mole) and epichlorohydrin (225 g) were mixed and allowed to stand three days at room temperature. The reaction mixture was heated at 140°-145° C. for 6 hrs. and then distilled under vacuum. The product (100 g) which boiled at 143° C. at 1.1 mmHg was recovered in 52% of the theoretical yield.

Workup

  1. temperatureThe reaction mixture was heated at 140°-145° C. for 6 hrs
  2. distillationand then distilled under vacuum
  3. customThe product (100 g) which boiled at 143° C. at 1.1 mmHg was recovered in 52% of the theoretical yield

Sources & evidence

ORD record
ord-6dd8cc6440c04a388d23121a4c921ddc
Source dataset
uspto-grants-1983_08
Patent number
US04400318

Linked notes

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