Trifluoroacetic acid → N-(1,2,3,4-tetrahydro-8-methoxy-5-nitro-2-naphthalenyl) acetamide

HRID 2058953Notes

Reaction equation

HRID 2058953 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][CH:10]([NH:13][C:14](=[O:16])[CH3:15])[CH2:9][CH2:8]2.FC(F)(F)C(O)=O.[N+:24]([O-])([O-:26])=[O:25].[Na+].C(=O)(O)[O-].[Na+]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:24]([O-:26])=[O:25])=[C:7]2[C:12]=1[CH2:11][CH:10]([NH:13][C:14](=[O:16])[CH3:15])[CH2:9][CH2:8]2

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 24268Sodium NitrateHCID 516892Sodium BicarbonateHCID 30189202-Acetamido-8-methoxytetralin

Product 1

HCID 12924809N-(1,2,3,4-tetrahydro-8-methoxy-5-nitro-2-naphthalenyl) acetamide

Procedure

A solution of 219 mg. (1 mmol) of N-(1,2,3,4-tetrahydro-8-methoxy-2-naphthalenyl) acetamide in 7.5 ml. of trifluoroacetic acid was treated with 140 mg. of sodium nitrate in one portion. It was stirred for one hour at room temperature, poured into excess sodium bicarbonate solution and extracted well with methylene chloride. The combined extracts were washed with water, dried and evaporated to give crystals. Recrystallization from ethyl acetate gave N-(1,2,3,4-tetrahydro-8-methoxy-5-nitro-2-naphthalenyl) acetamide as white crystals m.p. 205°-206°.

Workup

  1. extractionextracted well with methylene chloride
  2. washThe combined extracts were washed with water
  3. customdried
  4. customevaporated
  5. customto give crystals
  6. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-99e5604e076e4fe79ba25e1e0cb9c37b
Source dataset
uspto-grants-1982_03
Patent number
US04320148

Reaction notes

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