Acetic Acid → Methyl alpha-Methyl-1-nitro-1,2-dihydro-6-azanaphthalene-2-acetate

HRID 542994Notes

Reaction equation

HRID 542994 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:8]=[CH:9]2)([O-:3])=[O:2].[C:14](#N)[CH3:15].CN([S+](N(C)C)N(C)C)C.[CH3:27][Si-](F)(F)(C)C.[C:33](O)(=[O:35])C.[OH2:37]>CCCCCC>[CH3:27][CH:14]([CH:13]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[N:8][CH:9]=2)[CH:4]1[N+:1]([O-:3])=[O:2])[C:15]([O:35][CH3:33])=[O:37]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 962WaterHCID 6342AcetonitrileHCID 690855-NitroisoquinolineHCID 9795567Tris(dimethylamino)sulfonium difluorotrimethylsilicate

Product 1

HCID 13507926Methyl alpha-Methyl-1-nitro-1,2-dihydro-6-azanaphthalene-2-acetate

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A flame dried 50 mL flask fitted with an addition funnel was charged with 0.872 g (500 mmol) of 5-nitroisoquinoline and 0.95 mL (5.1 mmol) of MTS. An acetonitrile solution of 1.40 g (5.09 mmol) of TASF was slowly added to the reaction mixture in 15 min at -78° C. The mixture was stirred for 22 h at that temperature. One mL of acetic acid in 5 mL of hexane was added, and reaction was warmed to room temperature. After 30 min, 40 mL of water was added. The solid which precipitated out was collected and analyzed. The product yield was 0.972 g (74%). The product material was analyzed by infrared spectroscopy, nuclear magnetic resonance spectroscopy, and mass spectrometry.

Workup

  1. customA flame dried 50 mL flask
  2. customfitted with an addition funnel
  3. customreaction
  4. waitAfter 30 min
  5. customThe solid which precipitated out
  6. customwas collected

Sources & evidence

ORD record
ord-c487910042994acf854a10bc5a763356
Source dataset
uspto-grants-1987_04
Patent number
US04659862

Reaction notes

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