Dimethylamine → HCID 58418106, compound

HRID 1908820Notes

Reaction equation

HRID 1908820 reaction equation
Cl.Br[C:3]1[CH:8]=[C:7]([CH3:9])[N:6]=[C:5]([C:10]([OH:12])=[O:11])[CH:4]=1.[CH3:13][NH:14][CH3:15]>C(O)CCC>[CH3:13][N:14]([CH3:15])[C:3]1[CH:8]=[C:7]([CH3:9])[N:6]=[C:5]([C:10]([OH:12])=[O:11])[CH:4]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 67027005HCID 67027005, compound

Product 1

HCID 58418106HCID 58418106, compoundYield 142.9%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a solution of 4-bromo-6-methyl-pyridine-2-carboxylic acid hydrochloride (100 mg, 0.396 mmol) in butanol (6 mL), dimethylamine (162 mg, 1.19 mmol) is added and the mixture is refluxed for 2 days. The solvent is removed in vacuo and the residue is dried under HV to give 4-dimethylamino-6-methyl-pyridine-2-carboxylic acid (102 mg) as dimethylammonium salt in form of a yellow oil; LC-MS: tR=0.48 min, [M+1]+=181.07. This material is dissolved in DCM (5 mL), methanol (0.5 mL) and triethylamine (5 mL). The solution is stirred for 5 min at rt before it is concentrated and dried under HV to give the title compound (125 mg) as triethylammonium salt in form of a pale yellow oil. 1H NMR (D6-DMSO): δ 1.20 (t, J=7.3 Hz, 18H), 3.08 (q, J=7.0 Hz, 12H), 3.17 (s, 6H), 6.80 (s, 1H), 7.14 (s, 1H), 9.75 (s br, 2H).

Workup

  1. temperaturethe mixture is refluxed for 2 days
  2. customThe solvent is removed in vacuo
  3. customthe residue is dried under HV

Sources & evidence

ORD record
ord-0a36770dbb234acda20aafa54f37d81e
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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