Triethylamine → Methyl 5-chloro-2-methoxynicotinate

HRID 66588Notes

Reaction equation

HRID 66588 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]([OH:12])=[O:11])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[CH2:13](N(CC)CC)C>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]([O:12][CH3:13])=[O:11])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 98369735-Chloro-2-methoxynicotinic acid

Product 1

HCID 13282891Methyl 5-chloro-2-methoxynicotinate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

By the procedure of Example 1, 5-chloro-2-methoxypyridine-3-carboxylic acid [Sarges et al., J. Med. Chem. 19, 709 (1976); 10 g.] was converted to its acid chloride, which was added in one portion to 150 ml. of methanol (slight exotherm), then made basic with triethylamine (approximately 1.1 equivalents). The reaction mixture was evaporated to solids and the residue partitioned between ethyl acetate and water. The ethyl acetate layer was washed with fresh water and then brine, dried over anhydrous magnesium sulfate, filtered and evaporated to yield title product [9.75 g., m.p. 79°-81° C.; pnmr/CDCl3 /delta (ppm) 3.8 (s, 3H), 4.1 (s, 3H), 8.1 (d, 1H), 8.3 (d, 1H)].

Workup

  1. additionwas added in one portion to 150 ml
  2. customThe reaction mixture was evaporated to solids
  3. customthe residue partitioned between ethyl acetate and water
  4. washThe ethyl acetate layer was washed with fresh water
  5. dry with materialbrine, dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-a69d5544f5ee4944a6b3328f9908c18b
Source dataset
uspto-grants-1982_08
Patent number
US04342771

Reaction notes

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