Hydrochloric Acid → 2-(Diethylamino)-6-methylisonicotinic acid hydrochloride

HRID 2047270Notes

Reaction equation

HRID 2047270 reaction equation
C([O:3][C:4](=[O:17])[C:5]1[CH:10]=[C:9]([CH3:11])[N:8]=[C:7]([N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])[CH:6]=1)C.[ClH:18]>>[ClH:18].[CH2:15]([N:12]([CH2:13][CH3:14])[C:7]1[CH:6]=[C:5]([CH:10]=[C:9]([CH3:11])[N:8]=1)[C:4]([OH:17])=[O:3])[CH3:16]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 67026884HCID 67026884, compound

Product 1

HCID 670269722-(Diethylamino)-6-methylisonicotinic acid hydrochloride

Procedure

A solution of 2-diethylamino-6-methyl-isonicotinic acid ethyl ester (6.39 g, 27.0 mmol) in 6 N aq. HCl (100 mL) is stirred at 80° C. for 72 h before the solvent is removed in vacuo. The remaining solid is dried under high vacuum to give 2-diethylamino-6-methyl-isonicotinic acid hydrochloride (6.96 g) as a yellow solid; LC-MS: tR=0.53 min, [M+H]+=209.09; 1H NMR (D6-DMSO): δ 1.17 (t, J=6.8 Hz, 6H), 2.51 (s, 3H), 3.68 (q, J=6.3 Hz, 4H), 6.96 (s, 1H), 7.15 (s br, 1H).

Workup

  1. customis removed in vacuo
  2. customThe remaining solid is dried under high vacuum

Sources & evidence

ORD record
ord-bc2c89be17de4e28bdc118b7b5914452
Source dataset
uspto-grants-2013_11
Patent number
US08592460B2

Reaction notes

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