N-Methylisopropylamine → 2-(Isopropyl-methyl-amino)-6-methyl-isonicotinic acid

Reaction equation

Cl.[CH2:2]([N:4]([CH2:15][CH3:16])[C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([CH3:14])[N:13]=1)[C:8]([OH:10])=[O:9])C.[CH:17](NC)(C)C>>[CH:15]([N:4]([CH3:2])[C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([CH3:14])[N:13]=1)[C:8]([OH:10])=[O:9])([CH3:16])[CH3:17]

Participants

Reactant 2

HCID 78485N-Methylisopropylamine

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

Product 1

HCID 584180042-(Isopropyl-methyl-amino)-6-methyl-isonicotinic acid

Procedure

The title compound is prepared in analogy to 2-diethylamino-6-methyl-isonicotinic acid hydrochloride using isopropylmethylamine; LC-MS: tR=0.54 min; [M+H]+=209.09; 1H NMR δ 1.37 (d, J=6.3 Hz, 6H), 2.64 (s, 3H), 3.17 (s, 3H), 4.50-4.60 (m, 1H), 7.16 (s, 1H), 7.62 (s, 1H).

Sources & evidence

ORD record: ord-4e3582de711f43ed85392bb42a5ba029
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598208B2

Reaction notes

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