Sodium Nitrate → HCID 15744947, compound

HRID 327455Notes

Reaction equation

HRID 327455 reaction equation
[CH:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([Br:13])=[CH:10][CH:11]=2)[CH2:6][CH:5]([NH:14][CH:15]=[O:16])[CH2:4]1)=[O:2].[N+:17]([O-])([O-:19])=[O:18].[Na+]>FC(F)(F)C(O)=O>[CH:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([Br:13])=[CH:10][C:11]=2[N+:17]([O-:19])=[O:18])[CH2:6][CH:5]([NH:14][CH:15]=[O:16])[CH2:4]1)=[O:2]

Participants

4

Reactant 2

HCID 24268Sodium NitrateHCID 15937757HCID 15937757, compound

Product 1

HCID 15744947HCID 15744947, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of N-(1-formyl-6-bromo-1,2,3,4-tetrahydro-3-quinolyl)formamide (12.8 g, 45.2 mmol) and sodium nitrate (12.8 g, 150 mmol) in trifluoracetic acid (100 mL) was stirred at room temperature for 18 hours. The bulk of the solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and water. The ethyl acetate was washed with sodium hydroxide and water, and the ethyl acetate was removed to give 14.2 g of N-(1-formyl-6-bromo-1,2,3,4-tetrahydro-8-nitro-3-quinolyl)formamide (compound XXVIII) as a solid. This was dissolved in ethanolic hydrogen chloride (100 mL of 4.0 N), the mixture was refluxed for 1 hour, ether (200 mL) was added, and the precipitate was filtered off, washed with ether and dried to give 12.8 g (82% of 6-bromo-1,2,3,4-tetrahydro-8-nitro-3-quinolinamine dihydrochloride, mp >300° C.

Workup

  1. customThe bulk of the solvent was removed under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe ethyl acetate was washed with sodium hydroxide and water
  4. customthe ethyl acetate was removed

Sources & evidence

ORD record
ord-aa62f42d6c7f498baa334dab9e09924e
Source dataset
uspto-grants-1993_12
Patent number
US05273975

Reaction notes

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