Nitric Acid → 4-Nitro-5,6,7,8-tetrahydroquinoline 1-oxide

HRID 1613588Notes

Reaction equation

HRID 1613588 reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])(O)=[O:7].[N+:10]1([O-:20])[C:19]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=2[CH:13]=[CH:12][CH:11]=1>O>[N+:6]([C:13]1[C:14]2[CH2:15][CH2:16][CH2:17][CH2:18][C:19]=2[N+:10]([O-:20])=[CH:11][CH:12]=1)([O-:9])=[O:7]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 27781345,6,7,8-Tetrahydro-1-quinoliniumolate

Product 1

HCID 148359604-Nitro-5,6,7,8-tetrahydroquinoline 1-oxide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of sulphuric acid (200 ml) and nitric acid (200 ml) was treated with 5,6,7,8-tetrahydroquinoline N-oxide (47 g, 315 mmol), heated at 60°-80° for 3h, cooled to room temperature, poured onto ice (1 Kg), diluted with water (1 1), and extracted with dichloromethane (3×500 ml). The extracts were dried (MgSO4) and evaporated in vacuo to give the product (48 g) as an oil.

Workup

  1. additionpoured onto ice (1 Kg)
  2. extractionextracted with dichloromethane (3×500 ml)
  3. dry with materialThe extracts were dried (MgSO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-333db474aa3a47a6a6674157e1b80fc2
Source dataset
uspto-grants-1993_03
Patent number
US05194439

Reaction notes

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