Nitric Acid → HCID 13579642, compound

HRID 1380862Notes

Reaction equation

HRID 1380862 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][Cl:16])[C:9](=[O:17])[CH2:8][C:7]=2[CH:18]=1.C(=O)([O-])[O-].[K+].[K+].[N+:25]([O-])([OH:27])=[O:26]>>[N+:25]([C:4]1[C:3]([O:2][CH3:1])=[CH:18][C:7]2[CH2:8][C:9](=[O:17])[N:10]([CH2:13][CH2:14][CH2:15][Cl:16])[CH2:11][CH2:12][C:6]=2[CH:5]=1)([O-:27])=[O:26]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 11430Potassium CarbonateHCID 137469313-(3-Chloropropyl)-1,3,4,5-tetrahydro-8-methoxy-2H-3-benzazepin-2-one

Product 1

HCID 13579642HCID 13579642, compound

Procedure

First, 1-(8-methoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl)-3-chloropropane (28.5 g, 0.016 mol) is stirred into concentrated nitric acid (350 ml) for half an hour at 20°-25° C. The solution is then poured onto ice water, neutralized with potassium carbonate and extracted twice with methylene chloride. The extract is dried over magnesium sulphate, concentrated by evaporation in vacuo and the residue is purified over a silica gel column with ethyl acetate as eluant. Yield: 11 g. Mp: 127°-128° C.

Workup

  1. additionThe solution is then poured onto ice water
  2. extractionextracted twice with methylene chloride
  3. dry with materialThe extract is dried over magnesium sulphate
  4. concentrationconcentrated by evaporation in vacuo
  5. customthe residue is purified over a silica gel column with ethyl acetate as eluant

Sources & evidence

ORD record
ord-68fcb11acc7547bdbd249f5788475018
Source dataset
uspto-grants-1986_04
Patent number
US04584293

Reaction notes

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