6-(1-Ethyl-propyl)-4-methoxy-pyridine-2-carboxylic acid → 6-(1-Ethyl-propyl)-4-methyl-pyridine-2-carboxylic acid

HRID 2037316Notes

Reaction equation

HRID 2037316 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([O:10]C)=[O:9])[CH:5]=[C:4]([CH3:12])[CH:3]=1.[CH2:13]([CH:15](C1N=C(C(O)=O)C=C(OC)C=1)[CH2:16][CH3:17])[CH3:14]>>[CH2:13]([CH:15]([C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[C:4]([CH3:12])[CH:3]=1)[CH2:16][CH3:17])[CH3:14]

Participants

3

Reactant 2

HCID 686309506-(1-Ethyl-propyl)-4-methoxy-pyridine-2-carboxylic acidHCID 73553792Methyl 6-chloro-4-methylpicolinate

Product 1

HCID 686301606-(1-Ethyl-propyl)-4-methyl-pyridine-2-carboxylic acid

Procedure

Methyl 6-chloro-4-methyl-pyridine-2-carboxylate (500 mg, 2.69 mmol) is treated with 1-ethyl-propyl zinkbromide and saponified as described for 6-(1-ethyl-propyl)-4-methoxy-pyridine-2-carboxylic acid to give the title compound (220 mg) as a pale yellow oil; LC-MS**: tR=0.37 min, [M+1]+=208.29; 1H NMR (CDCl3): δ 0.80 (t, J=7.3 Hz, 6H), 1.69-1.81 (m, 4H), 2.48 (s, 3H), 2.58-2.67 (m, 1H), 7.21 (s, 1H), 7.91 (s, 1H).

Sources & evidence

ORD record
ord-e9d50eb943f1488fb4ec803b91787f49
Source dataset
uspto-grants-2013_11
Patent number
US08575200B2

Reaction notes

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