Oxalic Acid → HCID 20534873, compound

HRID 1156558Notes

Reaction equation

HRID 1156558 reaction equation
B#B.[CH2:3]([N:5]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH3:4].[C:27]([OH:32])(=[O:31])[C:28]([OH:30])=[O:29]>C(OCC)(=O)C>[C:27]([O-:32])(=[O:31])[C:28]([O-:30])=[O:29].[CH2:3]([NH+:5]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH3:4].[CH2:3]([NH+:5]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH3:4]

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 6328200DiboronHCID 12923064HCID 12923064, compound

Product 1

HCID 20534873HCID 20534873, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Reduction of the acylated amine was effected by reaction with diborane according to the procedure of Example 1. The reduced amine, N-ethyl-N-n-octyl-4-(4-nitrophenyl)butylamine, was converted to the oxalate salt by reaction with oxalic acid in ethyl acetate. After several recrystallizations from isopropanol there was recovered 3.9 g. of N-ethyl-N-n-octyl-4-(4-nitrophenyl)butylaminium oxalate. M.P. 105°-108° C.

Workup

  1. customAfter several recrystallizations from isopropanol
  2. customthere was recovered 3.9 g

Sources & evidence

ORD record
ord-593049329033491288b98c5f43e91386
Source dataset
uspto-grants-1982_06
Patent number
US04336269

Reaction notes

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