6-{2-[(Propan-2-yl)amino]propyl}pyridin-3-ol → 3-Pyridinol, 6-[2-[(1-methylethyl)amino]propyl]-, (2E)-2-butenedioate (1:1) (salt)

HRID 443409Notes

Reaction equation

HRID 443409 reaction equation
[CH:1]([NH:4][CH:5]([CH3:14])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][N:8]=1)([CH3:3])[CH3:2].[C:15]([OH:22])(=[O:21])/[CH:16]=[CH:17]/[C:18]([OH:20])=[O:19]>O>[C:15]([OH:22])(=[O:21])/[CH:16]=[CH:17]/[C:18]([OH:20])=[O:19].[CH:1]([NH:4][CH:5]([CH3:14])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][N:8]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 1313026-{2-[(Propan-2-yl)amino]propyl}pyridin-3-olHCID 444972Fumaric Acid

Product 1

HCID 678949723-Pyridinol, 6-[2-[(1-methylethyl)amino]propyl]-, (2E)-2-butenedioate (1:1) (salt)

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the suspension of 116 g of 2-(2-isopropylaminopropyl)-5-pyridinol and 310 ml of water, 65 g of fumaric acid are added while stirring at 70° under nitrogen. The resulting clear solution is stirred at 20° overnight, the precipitate formed filtered off and washed 3 times with 15 ml of cold water each. 873 g thereof (from several batches) are dissolved in 2,100 ml of water at 70°, the solution filtered hot and the filtrate stirred at room temperature under nitrogen for 2 days. The resulting suspension is filtered and the residue washed twice with 250 ml of cold water each, to yield the 2-(2-isopropylaminopropyl)-5-pyridinol monofumarate melting at 180°-183° with decomposition.

Workup

  1. additionare added
  2. stirringThe resulting clear solution is stirred at 20° overnight
  3. customthe precipitate formed
  4. filtrationfiltered off
  5. washwashed 3 times with 15 ml of cold water each
  6. dissolution873 g thereof (from several batches) are dissolved in 2,100 ml of water at 70°
  7. filtrationthe solution filtered hot
  8. stirringthe filtrate stirred at room temperature under nitrogen for 2 days
  9. filtrationThe resulting suspension is filtered
  10. washthe residue washed twice with 250 ml of cold water each,

Sources & evidence

ORD record
ord-c521157f2d814d0c9c8298d3e47a2f1f
Source dataset
uspto-grants-1981_04
Patent number
US04260619

Reaction notes

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