Quinoline → HCID 54439373, compound

HRID 2057652Notes

Reaction equation

HRID 2057652 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:17][CH:16]=2)=[CH:4][CH:3]=1.N1C2C(=CC=CC=2)C=CC=1>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]2[CH:16]=[CH:17][C:18]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:19][CH:20]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7047QuinolineHCID 20331233HCID 20331233, compound

Product 1

HCID 54439373HCID 54439373, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 10.0 g. ethyl 4-[6-(4-chlorophenyl)hexa-5-ynylamino]phenylacetate in 75 ml. acetone is added 1.0 ml. quinoline and 0.2 g. of palladium-on-calcium carbonate. The solution is hydrogenated at slightly above atmospheric pressure until 600 ml. hydrogen has been absorbed. The catalyst is filtered and washed with several small portions of acetone. The organic solution is diluted with 200 ml. water, the precipitate is collected, dried, and recrystallized from acetonitrile to yield the title compound as white crystals.

Workup

  1. customhydrogen has been absorbed
  2. filtrationThe catalyst is filtered
  3. washwashed with several small portions of acetone
  4. additionThe organic solution is diluted with 200 ml
  5. customwater, the precipitate is collected
  6. customdried
  7. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-21838f2ba9814648acd9f486ecf51015
Source dataset
uspto-grants-1980_07
Patent number
US04211783

Reaction notes

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