Water → HCID 19822144, compound

HRID 1030195Notes

Reaction equation

HRID 1030195 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)=[C:5]2[C:10](=[C:11]([N+:13]([O-])=O)[CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[CH3:16].O(CCCC)CCCC.O>[Fe].CC(O)=O>[NH2:13][C:11]1[CH:12]=[C:3]([O:2][CH3:1])[C:4]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)=[C:5]2[C:10]=1[N:9]=[CH:8][CH:7]=[C:6]2[CH3:16]

Participants

6

Reactant 3

HCID 962WaterHCID 8909Butyl etherHCID 53923883HCID 53923883, compound

Product 1

HCID 19822144HCID 19822144, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

A mechanically stirred mixture of 6-methoxy-4-methyl-8-nitro-5-[5-(thienyl) pentoxy] quinoline (5.50 g, 0.014 mol), Fe-filings (6 g), Bu2O (15 ml), H2O (50 ml) and HOAc (1.5 ml) was heated at 105°-110° C. for 2.5 h, allowed to cool and filtered. The residue was well washed with Et2O (200 ml) and the filtrate and the washings were combined. The organic layer was separated and the aqueous layer was extracted with Et2O (2×75 ml). The combined organic layers were washed with saturated NaCl solution (2×50 ml), dried (K2CO3), treated with carbon (Darco G-60), and concentrated to a yellow oil which on trituration with pet. ether (20°-40° C., 20 ml), at -20° C., gave 8-amino-6-methoxy-4-methyl-5-[5-(2-thienyl)pentoxy] quinoline as a yellow solid, 4.07 g (80%), m.p. 42°-44° C. This material was used without further purification.

Workup

  1. temperaturewas heated at 105°-110° C. for 2.5 h
  2. temperatureto cool
  3. filtrationfiltered
  4. washThe residue was well washed with Et2O (200 ml)
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with Et2O (2×75 ml)
  7. washThe combined organic layers were washed with saturated NaCl solution (2×50 ml)
  8. dry with materialdried (K2CO3)
  9. additiontreated with carbon (Darco G-60)
  10. concentrationconcentrated to a yellow oil which on trituration with pet. ether (20°-40° C., 20 ml), at -20° C.

Sources & evidence

ORD record
ord-2c97b50289ce43b2a5a8fbd511accb79
Source dataset
uspto-grants-1992_04
Patent number
US05104885

Reaction notes

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