N-Methylethylamine → 2-Ethyl-6-(ethyl-methyl-amino)-isonicotinic acid

HRID 2047279Notes

Reaction equation

HRID 2047279 reaction equation
[CH2:1]([N:3]([CH2:14][CH3:15])[C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([CH3:13])[N:12]=1)[C:7]([OH:9])=[O:8])C.Cl[C:17]1C=C(C=C(Cl)N=1)C(O)=O.C(NC)C>>[CH2:13]([C:11]1[CH:10]=[C:6]([CH:5]=[C:4]([N:3]([CH2:14][CH3:15])[CH3:1])[N:12]=1)[C:7]([OH:9])=[O:8])[CH3:17]

Participants

4

Reactant 3

HCID 12219N-MethylethylamineHCID 948302,6-Dichloroisonicotinic acidHCID 584180552-(Diethylamino)-6-methylisonicotinic acid

Product 1

HCID 584180162-Ethyl-6-(ethyl-methyl-amino)-isonicotinic acid

Procedure

The title compound is prepared in analogy to 2-diethylamino-6-methyl-isonicotinic acid starting from 2,6-dichloro-isonicotinic acid and N-ethyl-N-methylamine; LC-MS: tR=0.56 min, [M+1]+=209.09; 1H NMR (D6-DMSO): δ 1.16 (t, J=7.0 Hz, 3H), 1.24 (t, J=7.3 Hz, 3H), 2.95 (q, J=7.5 Hz, 2H), 3.57 (s, 3H), 3.76 (q, J=6.8 Hz, 2H), 6.98 (s, 1H), 7.23 (s, 1H).

Sources & evidence

ORD record
ord-76ab51ef58c34a66a115381c687b3e70
Source dataset
uspto-grants-2013_11
Patent number
US08592460B2

Reaction notes

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