Hydrochloric Acid → 2-(2-t-Butylaminopropyl)-5-pyridinol dihydrochloride

HRID 443408Notes

Reaction equation

HRID 443408 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.[C:9]([N:13]=[CH:14][CH3:15])([CH3:12])([CH3:11])[CH3:10].[ClH:16]>O1CCCC1.C([Li])CCC.C(OCC)(=O)C>[ClH:16].[ClH:16].[C:9]([NH:13][CH:14]([CH3:15])[CH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1)([CH3:12])([CH3:11])[CH3:10]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 142752-Methyl-5-hydroxypyridineHCID 138901N-Ethylidene-2-methylpropan-2-amine

Product 1

HCID 234671372-(2-t-Butylaminopropyl)-5-pyridinol dihydrochloride

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 178418339ButyllithiumSolvent

Procedure

To the suspension of 9.8 g of 2-methyl-5-pyridinol in 200 ml of tetrahydrofuran, 135 ml of 1.6 molar n-butyllithium are added during 30 minutes while stirring under nitrogen at -20°. After 3 hours 10 g of t-butyliminoethane are added during 30 minutes at said temperature and the resulting mixture is processed as described in Example 4, except that the final solution is acidified with hydrogen chloride in ethyl acetate, to yield the 2-(2-t-butylaminopropyl)-5-pyridinol dihydrochloride melting at 218°-220°.

Workup

  1. additionare added during 30 minutes

Sources & evidence

ORD record
ord-37d30f05e6bf446da9a704874e36a680
Source dataset
uspto-grants-1981_04
Patent number
US04260619

Reaction notes

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