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

HRID 1461286Notes

Reaction equation

HRID 1461286 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-29b71222762b4378b5653430cb999698
Source dataset
uspto-grants-1991_12
Patent number
US05075303

Reaction notes

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