Acetic Acid → HCID 615721, compound

HRID 1863107Notes

Reaction equation

HRID 1863107 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[C:8]([N+:17]([O-])=O)[CH:9]=[C:10]([O:15][CH3:16])[CH:11]=2)[N:6]=1)(=[O:3])[CH3:2].C(O)(=O)C>[Fe].O>[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[C:8]([NH2:17])[CH:9]=[C:10]([O:15][CH3:16])[CH:11]=2)[N:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 20393434HCID 20393434, compound

Product 1

HCID 615721HCID 615721, compoundYield 78.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A mixture of 10.5 g (0.04 mole) of crude 2-acetamido-6-methoxy-8-nitroquinoline, 14 g of iron filings, 2 ml of glacial acetic acid, and 120 ml of water was stirred on the steam bath for 18 hr. The mixture was filtered and the solid residue was washed thoroughly with acetone. The acetone washings were concentrated and the residue was eluted through a short silica gel column with methylene chloride to give 7.3 g (78%) of 2-acetamido-8-amino-6-methoxyquinoline. A sample recrystallized from 95% ethanol melted at 192°-194°.

Workup

  1. filtrationThe mixture was filtered
  2. washthe solid residue was washed thoroughly with acetone
  3. concentrationThe acetone washings were concentrated
  4. washthe residue was eluted through a short silica gel column with methylene chloride

Sources & evidence

ORD record
ord-1a3b141f6987432b941c8b8ddbe5728b
Source dataset
uspto-grants-1979_09
Patent number
US04167638

Reaction notes

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