Acetic Acid → 3-Hydroxymethylbenzamidinium acetate

HRID 925487Notes

Reaction equation

HRID 925487 reaction equation
CC1O[N:5]=[C:4]([C:7]2[CH:8]=[C:9]([CH2:13][OH:14])[CH:10]=[CH:11][CH:12]=2)[N:3]=1.[C:15]([OH:18])(=[O:17])[CH3:16].O.[H][H]>[Ni].CO>[C:15]([O-:18])(=[O:17])[CH3:16].[OH:14][CH2:13][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=1)[C:4]([NH2:5])=[NH2+:3]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 7060550[3-(5-Methyl-1,2,4-oxadiazol-3-yl)phenyl]methanolHCID 178418361HCID 178418361, compound

Product 1

HCID 674482713-Hydroxymethylbenzamidinium acetate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

40 g of Raney nickel (water-wet) are added to 124.84 g of [3-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]methanol (569.39 mmol) in a mixture of 1300 ml of methanol, 100 ml of glacial acetic acid and 100 ml of water, and the mixture is hydrogenated at room temperature and atmospheric pressure until 14.7 l of hydrogen have been taken up (45 h). For work-up, the catalyst is filtered off, and the solution which remains is evaporated to dryness, and the residue is boiled up in methyl tert-butyl ether and filtered off. The crystals are dried overnight in vacuo.

Workup

  1. customis hydrogenated at room temperature
  2. custom(45 h)
  3. filtrationFor work-up, the catalyst is filtered off
  4. customthe solution which remains is evaporated to dryness
  5. filtrationfiltered off
  6. customThe crystals are dried overnight in vacuo

Sources & evidence

ORD record
ord-ddaa8b1787594dd1b702e2541c9b982a
Source dataset
uspto-grants-2016_03
Patent number
US09284300B2

Reaction notes

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