Isonicotinic Acid → HCID 21505011, compound

HRID 1287545Notes

Reaction equation

HRID 1287545 reaction equation
[CH2:1]([O:8][C:9](=[O:16])[CH:10](Br)[CH2:11][CH:12]([CH3:14])[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([OH:25])(=[O:24])[C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1.CN(C)C=O>C(N(CC)CC)C>[CH2:1]([O:8][C:9](=[O:16])[CH:10]([O:25][C:17](=[O:24])[C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1)[CH2:11][CH:12]([CH3:14])[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 5922Isonicotinic AcidHCID 6228DimethylformamideHCID 21707506Benzyl 2-bromo-4-methylpentanoate

Product 1

HCID 21505011HCID 21505011, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A total of 29.5 g of benzyl-(RS)-α-bromo-isocaproate was added dropwise at 60° with stirring over a period of 15 minutes to a solution of 12.8 g of isonicotinic acid in a mixture of 60 ml. of dimethyl-formamide and 14.8 ml of triethylamine. The reaction mixture was stirred for 5 hours at 90°. The triethylamine hydrobromide was then filtered off by suction and the filtrate evaporated under reduced pressure at 60°. The residue was dissolved in 100 ml of ethyl acetate and filtered and the filtrate washed three times with 15 ml portions of 1-N potassium bicarbonate solution and twice with 20 ml portions of water. The ethyl acetate solution was dried with magnesium sulphate and evaporated under reduced pressure at 45°. Benzyl-(RS)-2-(isonicotinoyloxy)-isocaproate was obtained as an oil.

Workup

  1. filtrationThe triethylamine hydrobromide was then filtered off by suction
  2. customthe filtrate evaporated under reduced pressure at 60°
  3. dissolutionThe residue was dissolved in 100 ml of ethyl acetate
  4. filtrationfiltered
  5. washthe filtrate washed three times with 15 ml portions of 1-N potassium bicarbonate solution
  6. dry with materialThe ethyl acetate solution was dried with magnesium sulphate
  7. customevaporated under reduced pressure at 45°

Sources & evidence

ORD record
ord-b54aeeb3298c4e7a84d71eef4e30147c
Source dataset
uspto-grants-1976_10
Patent number
USRE029003

Reaction notes

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