HCID 627786, compound → HCID 618016, compound

HRID 1863101Notes

Reaction equation

HRID 1863101 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([N+:14]([O-])=O)[CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([C:17]([F:20])([F:19])[F:18])[CH:3]=1>[Pd].C(O)C>[NH2:14][C:7]1[CH:8]=[C:9]([O:12][CH3:13])[CH:10]=[C:11]2[C:6]=1[N:5]=[C:4]([C:17]([F:18])([F:19])[F:20])[CH:3]=[CH:2]2

Participants

4

Reactant 1

HCID 627786HCID 627786, compound

Product 1

HCID 618016HCID 618016, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3.1 g of (0.01 mole) of 4-chloro-6-methoxy-8-nitro-2-trifluoromethylquinoline, 75 ml of ethanol and 1 g of 5% Pd on CaCO3 was shaken on a Parr apparatus for 4.5 hr, at 50°-60°, under a hydrogen pressure of 70 psig. The yellow mixture was filtered and concentrated to dryness in vacuo. The residue was extracted with boiling ligroine (bp 90°-120° ) and the solvent was removed from the extract under reduced pressure. The residue was distilled to give 1.25 g (52%) of 8-amino-6-methoxy-2-trifluoromethylquinoline as a yellow oil, bp 127°-128° /1 mm.

Workup

  1. filtrationThe yellow mixture was filtered
  2. concentrationconcentrated to dryness in vacuo
  3. extractionThe residue was extracted
  4. customthe solvent was removed from the
  5. extractionextract under reduced pressure
  6. distillationThe residue was distilled

Sources & evidence

ORD record
ord-413fdba3c55b4707a1947b20af3ed10c
Source dataset
uspto-grants-1979_09
Patent number
US04167638

Reaction notes

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