Ammonium Hydroxide → HCID 19027054, compound

HRID 1090077Notes

Reaction equation

HRID 1090077 reaction equation
[OH-].[NH4+].[C:3]([NH:10][C:11]1[C:20]([N+:21]([O-:23])=O)=[CH:19][CH:18]=[C:17]2[C:12]=1[CH2:13][CH2:14][CH2:15][CH2:16]2)([C:5](OCC)=[O:6])=[O:4]>O.CN(C)C=O.O1CCCC1.[Pt]>[OH:23][N:21]1[C:20]2[CH:19]=[CH:18][C:17]3[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=3[C:11]=2[NH:10][C:3](=[O:4])[C:5]1=[O:6]

Participants

7

Reactant 2

HCID 14923Ammonium HydroxideHCID 19027068HCID 19027068, compound

Product 1

HCID 19027054HCID 19027054, compoundYield 47.4%

Reagents, catalysts & solvents 4

HCID 23939PlatinumCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 25% ammonium hydroxide in water (0.7 ml) was added to a solution of 5-ethoxalylamino-1,2,3,4-tetrahydro-6-nitronaphthalene (0.30 g, 1 mmol) in a mixture of 10 ml of N,N-dimethylformamide and 30 ml of tetrahydrofuran. The mixture was hydrogenated at atmospheric pressure and room temperature in the presence of 5% platinum on carbon, until the starting material had disappeared. The mixture was filtered and the filtrate was discarded. Now the filter was washed with 5% aqueous potassium hydroxide, and the filtrate was acidified with 4N hydrochloric acid. The white precipitate was isolated by filtration and washed with water and ethanol to give 0.11 g (46%) of the title compound. M.p. >225° C. dec.; 1H-NMR (DMSO-d6): 1.57-1.90 (m, 4H, 2CH2), 2.50-2.93 (m, 4H, 2CH2), 6.95 (d, J=9 Hz, 1H, ArH), 7.30 (d, J=9 Hz, 1H, ArH); appr. 11.1 (very broad s, 1H, NH); IR (KBr): 1670 cm-1 ; MS (m/e): 232 (M+, 87%).

Workup

  1. filtrationThe mixture was filtered
  2. washNow the filter was washed with 5% aqueous potassium hydroxide
  3. customThe white precipitate was isolated by filtration
  4. washwashed with water and ethanol

Sources & evidence

ORD record
ord-fdfaf3de83d543a4b58c5827b2676560
Source dataset
uspto-grants-1992_01
Patent number
US05081123

Reaction notes

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