7-Ethoxy-8-nitroquinoline → 8-Amino-7-ethoxyquinoline

HRID 34456Notes

Reaction equation

HRID 34456 reaction equation
[CH2:1]([O:3][C:4]1[C:13]([N+:14]([O-])=O)=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1)[CH3:2]>C(O)C.[Pd]>[NH2:14][C:13]1[C:4]([O:3][CH2:1][CH3:2])=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[CH:8]2

Participants

4

Reactant 1

HCID 128498157-Ethoxy-8-nitroquinoline

Product 1

HCID 128498168-Amino-7-ethoxyquinoline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

7-Ethoxy-8-nitroquinoline (2.62 g, 12.0 mmole), in absolute ethanol (200 mL) was shaken with 10% palladium on carbon (0.10 g) under hydrogen (50 psi) for 3 hr. The catalyst was filtered off and the filtrate concentrated to 10 mL. The title compound crystallized as yellow needles (1.86 g, 82%); mp 94°-95°. Anal. Calcd for C11H12N2O: C, 70.19; H, 6.43; N, 14.88. Found: C, 70.16; H, 6.47; N, 14.87.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate concentrated to 10 mL
  3. customThe title compound crystallized as yellow needles (1.86 g, 82%)

Sources & evidence

ORD record
ord-3cfdff233b3f4a608e8a60aba5bb463f
Source dataset
uspto-grants-1988_08
Patent number
US04761475

Reaction notes

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