Water → HCID 19822143, compound

HRID 1030198Notes

Reaction equation

HRID 1030198 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][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[C:14]([CH3:27])=[CH:15][CH:16]=[N:17]2.O(CCCC)CCCC.O>[Fe].CC(O)=O>[NH2:24][C:19]1[CH:20]=[C:21]([O:22][CH3:23])[C:12]([O:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[C:14]2[CH3:27]

Participants

6

Reactant 3

HCID 962WaterHCID 8909Butyl etherHCID 19822136HCID 19822136, compound

Product 1

HCID 19822143HCID 19822143, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

A mechanically stirred mixture of 5-[5-(2-furyl)pentoxy]-6-methoxy-4-methyl-8-nitroquinoline (2.20 g, 0.0059 mol), Fe-filings (3.0 g), Bu2O (8 ml), H2O (30 ml) and HOAc (0.5 ml) was heated at 95°-100° C. for 2 h, allowed to cool and filtered. The residue was washed with Et2O (100 ml) and the filtrate and the washings were combined. The organic layer was separated and the aqueous layer was extracted with Et2O (2×50 ml). The combined organic layers were washed with saturated NaCl solution (1×50 ml), dried (Na2SO4), treated with Darco and concentrated to an oil which on trituration with cold hexane produced 8-amino-5-[5-(2-furyl) pentoxy]-6-methoxy-4-methylquinoline as a crude greenish-yellow solid 1.35 g (65%), mp 41°-42° C. This material was used without further purification.

Workup

  1. temperaturewas heated at 95°-100° C. for 2 h
  2. temperatureto cool
  3. filtrationfiltered
  4. washThe residue was washed with Et2O (100 ml)
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with Et2O (2×50 ml)
  7. washThe combined organic layers were washed with saturated NaCl solution (1×50 ml)
  8. dry with materialdried (Na2SO4)
  9. additiontreated with Darco
  10. concentrationconcentrated to an oil which on trituration with cold hexane

Sources & evidence

ORD record
ord-7d1b33cada1547299e1755edda8a3ba5
Source dataset
uspto-grants-1992_04
Patent number
US05104885

Reaction notes

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