Acetic Acid → 8-Amino-5-decoxy-6-methoxyquinoline

HRID 1583810Notes

Reaction equation

HRID 1583810 reaction equation
[CH2:1]([O:11][C:12]1[C:21]([O:22][CH3:23])=[CH:20][C:19]([N+:24]([O-])=O)=[C:18]2[C:13]=1[CH:14]=[CH:15][CH:16]=[N:17]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C(OCCCC)CCC.C(O)(=O)C>[Fe].O>[NH2:24][C:19]1[CH:20]=[C:21]([O:22][CH3:23])[C:12]([O:11][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[CH:14]2

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8909Butyl etherHCID 135359345-Decoxy-6-methoxy-8-nitroquinoline

Product 1

HCID 135359528-Amino-5-decoxy-6-methoxyquinolineYield 83.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A stirred mixture of 4.7 g (0.013 mole) of 5-decoxy-6-methoxy-8-nitroquinoline, 12 g of degreased 40 mesh iron filings, 6 ml of butyl ether, 6 ml of acetic acid and 30 ml of water was heated at 100° for 2 hr, cooled and filtered. The solid was washed with water, dried and extracted with diethyl ether. Evaporation of the diethyl ether, solution of the residue in petroleum ether (20°-40°) and cooling in Dry-Ice acetone gave 3.6 g of pale green solid. Two crystallizations from petroleum ether (20°-40°) (carbon) provided 2.3 g (54%) of amino compound as yellow-green solid, mp 65°.

Workup

  1. temperaturewas heated at 100° for 2 hr
  2. temperaturecooled
  3. filtrationfiltered
  4. washThe solid was washed with water
  5. customdried
  6. extractionextracted with diethyl ether
  7. customEvaporation of the diethyl ether, solution of the residue in petroleum ether (20°-40°)
  8. temperaturecooling in Dry-Ice acetone

Sources & evidence

ORD record
ord-f62ebdd1613d4c1cac61c757ea705fc2
Source dataset
uspto-grants-1985_11
Patent number
US04554279

Reaction notes

Loading…