Dimethylformamide → HCID 19874055, compound

HRID 465321Notes

Reaction equation

HRID 465321 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([N+:22]([O-:24])=O)[C:7]([NH:14][C:15]([C:17](OCC)=[O:18])=[O:16])=[C:8]2[C:13]=1[CH2:12][CH2:11][CH2:10][CH2:9]2)(=[O:3])[CH3:2].CN(C)C=O>C(O)C.[Pt]>[C:1]([C:4]1[C:13]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=2[C:7]2[NH:14][C:15](=[O:16])[C:17](=[O:18])[N:22]([OH:24])[C:6]=2[CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 19027064HCID 19027064, compound

Product 1

HCID 19874055HCID 19874055, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

A solution of 8-acetyl-5-ethoxalylamino-1,2,3,4-tetrahydro-6-nitronaphthalene (0.67 g, 2 mmol) in 100 ml of ethanol was hydrogenated at room temperature and atmospheric pressure over 50 mg of 5% platinum on carbon for 1 h. Then 50 ml of N,N-dimethylformamide was added to dissolve the precipitated solid, and the catalyst was removed by filtration. The filtrate was concentrated and the residue was washed with 50 ml of ethanol to give 0.40 g (73%) of the title compound. M.p. >200° C. decomp. (DSC); IR (KBr): 1709, 1677 cm1, 1H-NMR (DMSO-d6): 1.43-1.93 (m, 4H, 2CH2), 2.57 (s, 3H, COCH3), 2.53-3.07 (m, 4H, 2CH2), 7.57 (s, 1H, H-7), 11.4 (very broad s, 2H, OH and NH); MS (m/e: 274 (M+, 100%).

Workup

  1. customwas hydrogenated at room temperature
  2. dissolutionto dissolve the precipitated solid
  3. customthe catalyst was removed by filtration
  4. concentrationThe filtrate was concentrated
  5. washthe residue was washed with 50 ml of ethanol

Sources & evidence

ORD record
ord-0f01748fad2c49f4a3d756daec53ee15
Source dataset
uspto-grants-1992_10
Patent number
US05153195

Reaction notes

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