(2-Thienylmethyl)amine → 5-Methyl-2-[1-(2-thienylmethylamino)methyl]-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one

HRID 1900751Notes

Reaction equation

HRID 1900751 reaction equation
Br[CH2:2][CH:3]1[O:17][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH2:4]1)[NH:11][C:10](=[O:16])[CH:9]=[CH:8]3.[NH2:18][CH2:19][C:20]1[S:21][CH:22]=[CH:23][CH:24]=1>>[CH3:15][C:13]1[CH:14]=[C:5]2[CH2:4][CH:3]([CH2:2][NH:18][CH2:19][C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)[O:17][C:6]2=[C:7]2[C:12]=1[NH:11][C:10](=[O:16])[CH:9]=[CH:8]2

Participants

3

Reactant 2

HCID 34005(2-Thienylmethyl)amineHCID 233696452-Bromomethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one

Product 1

HCID 233695645-Methyl-2-[1-(2-thienylmethylamino)methyl]-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-oneYield 83.1%

Conditions

Temperature
150 °C

Procedure

A mixture of 2-bromomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one (2.942 g) and 2-aminomethylthiophene (4.528 g) was stirred in a hot bath at 150° C. in the stream of argon gas for 4 hours. The solvent was distilled off under reduced pressure. Chloroform was added to the residue, and washed with sodium bicarbonate water, and water in this order. After dried, the residue was crystallized from ethanol to obtain 2.712 g of a free base of the title compound as pale yellow prisms (mp.: 163°-165° C.).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionChloroform was added to the residue
  3. washwashed with sodium bicarbonate water, and water in this order
  4. customAfter dried
  5. customthe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-d420fefcee6c46ea91a4cc7be8b1494d
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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