Phosphoric Acid → m-Aminobenzylamine phosphoric acid salt

HRID 580086Notes

Reaction equation

HRID 580086 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[CH:7]=[N:8]O)([O-])=O.[P:13](=[O:17])([OH:16])([OH:15])[OH:14].[H][H]>[Pt].C(O)C(C)C>[P:13](=[O:14])([OH:17])([OH:16])[OH:15].[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[CH2:7][NH2:8]

Participants

6

Reactant 3

HCID 1004Phosphoric AcidHCID 2191323-NitrobenzaldoximeHCID 178418361HCID 178418361, compound

Product 1

HCID 20136024m-Aminobenzylamine phosphoric acid saltYield 86.1%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6560IsobutanolSolvent

Procedure

33.2 g (0.2 mol) of this m-nitrobenzaldoxime, 70 g (0.35 mol) of a 50% aqueous solution of phosphoric acid, 0.3 g of a 10% Pt-C catalyst and 300 ml of isobutanol were charged into a hermetically sealed glass container and vigorously stirred while charging hydrogen. Reaction was continued at temperatures of 25° to 30° C. for 18 hours and 23 l of hydrogen was absorbed. The reaction mixture from which crystals deposited was filtered and 54.8 g of crude m-aminobenzylamine phosphoric acid salt (yield 86.1%) was obtained. This crude m-aminobenzylamine phosphoric acid salt was recrystallized from a 50% methanol-water solution and pure m-aminobenzylamine phosphoric acid salt of white and flaky crystals was obtained. M.P. 210°-213° C.

Workup

  1. customReaction
  2. custom23 l of hydrogen was absorbed
  3. filtrationThe reaction mixture from which crystals deposited was filtered

Sources & evidence

ORD record
ord-08575de4e6da4cee95441ab564e25e18
Source dataset
uspto-grants-1988_06
Patent number
US04751328

Reaction notes

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