Ammonia → HCID 19027061, compound

HRID 1032942Notes

Reaction equation

HRID 1032942 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([N+:16]([O-:18])=[O:17])[C:7](OC)=[C:8]2[C:13]=1[CH2:12][CH2:11][CH2:10][CH2:9]2)(=[O:3])[CH3:2].[NH3:19]>CS(C)=O>[C:1]([C:4]1[CH:5]=[C:6]([N+:16]([O-:18])=[O:17])[C:7]([NH2:19])=[C:8]2[C:13]=1[CH2:12][CH2:11][CH2:10][CH2:9]2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 19027049HCID 19027049, compound

Product 1

HCID 19027061HCID 19027061, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 8-acetyl-1,2,3,4-tetrahydro-5-methoxy-6nitronaphthalene (1.0 g, 4 mmol) in 15 ml of dry dimethylsulfoxide was heated to 100° C. and ammonia was passed into the solution for 3 h. After the solution was added to 100 ml of ice-water, the crude solid was filtered off and washed with water. Recrystallization from ethanol afforded 0.71 g (75%) of the pure title compound M.p. 170°-172° C.; 1H-NMR (DMSO-d6): 1.47-1.93 (m, 4H, 2CH2), 2.27-2.63 (m, 2H, CH2), 2.48 (s, 3H, COCH3), 2.70-3.03 (m, 2H, CH2), 7.50 (broad s, 2H, NH2), 8.33 (s, 1H, H-7).

Workup

  1. filtrationthe crude solid was filtered off
  2. washwashed with water
  3. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-7b7a768bdd21440f8bb915a21e07c979
Source dataset
uspto-grants-1994_05
Patent number
US05308845

Reaction notes

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