Acetic Acid → 6-Methoxy-1,2,3,4-tetrahydro-8-quinolinylamine

HRID 256305Notes

Reaction equation

HRID 256305 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([N+:13]([O-])=O)[CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.C(O)(=O)C.[OH-].[Na+]>CO.O=[Pt]=O>[NH2:13][C:11]1[CH:12]=[C:3]([O:2][CH3:1])[CH:4]=[C:5]2[C:10]=1[NH:9][CH2:8][CH2:7][CH2:6]2

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 68226-Methoxy-8-nitroquinolineHCID 14798Sodium Hydroxide

Product 1

HCID 218172006-Methoxy-1,2,3,4-tetrahydro-8-quinolinylamine

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalyst2×HCID 887MethanolSolvent

Procedure

A suspension of 6-methoxy-8-nitroquinoline (20 g, 98 mmol) in methanol (200 ml) was hydrogenated over PtO2 (0.5 g) at 50 p.s.i. for 2.5 hours. The solution was treated with acetic acid (11.5 ml, 200 mmol) and PtO2 (0.5 g) and hydrogenated at 50 p.s.i. for 18 hours. The catalyst was removed by filtration and the solution evaporated in vacuo to give an oil. The residue was basified with 1 N-sodium hydroxide (200 ml) and the aqueous mixture extracted with diethyl ether (2×200 ml). The extracts were dried (MgSO4) and evaporated in vacuo to give crude 8-amino-1,2,3,4-tetrahydro-6-methoxyquinoline as a red oil.

Workup

  1. waitfor 18 hours
  2. customThe catalyst was removed by filtration
  3. customthe solution evaporated in vacuo
  4. customto give an oil
  5. extractionthe aqueous mixture extracted with diethyl ether (2×200 ml)
  6. dry with materialThe extracts were dried (MgSO4)
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-7e2d54e2e4dd4a029b825f77e4592006
Source dataset
uspto-grants-1987_10
Patent number
US04703044

Reaction notes

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