2-Amino-2-methyl-1-propanol → 3-Pyridinecarboxamide, N-(2-hydroxy-1,1-dimethylethyl)-

HRID 259093Notes

Reaction equation

[C:1]([O:9]CC)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[NH2:12][C:13]([CH3:17])([CH3:16])[CH2:14][OH:15]>>[OH:15][CH2:14][C:13]([NH:12][C:1](=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1)([CH3:17])[CH3:16]

Participants

Reactant 2

HCID 118072-Amino-2-methyl-1-propanol

HCID 69188Ethyl Nicotinate

Product 1

HCID 101040833-Pyridinecarboxamide, N-(2-hydroxy-1,1-dimethylethyl)-

Procedure

100 g (0.66 mol) Ethyl nicotinate and 88g (0.99 mol) 2-amino-2-methyl-1propanol were mixed and heated together under reflux for 2 hours. The excess amino alcohol was removed by distillation, bp 50°-60° (1mm). The yellow residue was recrystallized from ether-acetone to give 87.3 g (0.45 mol), 68%, N-(1-hydroxy-2-methyl-2-propyl) nicotinamide, mp 91°-93°; ir (KBr) 3385, 3200, 1665, and 1590 cm-1 ; pmr (CDCl3) δ 8.8 - 7.3 (m, 4H), 6.7 (bs, 1H), 5.0 (s, 1H), 3.7 (s, 2H) and 1.4 (s, 6H) ppm.

Workup

temperatureheated together
temperatureunder reflux for 2 hours
customThe excess amino alcohol was removed by distillation, bp 50°-60° (1mm)
customThe yellow residue was recrystallized from ether-acetone

Sources & evidence

ORD record: ord-6adfe72d49e442f894c62a37515c983d
Source dataset: uspto-grants-1977_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04036843

Reaction notes

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