Acetic Acid → HCID 118117479, compound

HRID 2279934Notes

Reaction equation

HRID 2279934 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:8]([C:10]1[N:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[CH:12][CH:11]=1)=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[C:2]1([NH:1][CH2:8][C:10]2[N:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[CH:12][CH:11]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6115AnilineHCID 5049666Sodium triacetoxyborohydrideHCID 12575850Methyl 6-formylpyridine-2-carboxylate

Product 1

HCID 118117479HCID 118117479, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of aniline (128 mg, 1.38 mmol), methyl 6-formylpyridine-2-carboxylate (217 mg, 1.31 mmol) and acetic acid (75 μL, 1.31 mmol) in dichloromethane (10 mL) was stirred at room temperature for 24 h. After this time, sodium triacetoxyborohydride (695 mg, 3.28 mmol) was added in one portion and the resulting mixture was stirred at room temperature for 18 h. The reaction was partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution. The organic layer was washed with brine, passed through a hydrophobic fit and the solvent was removed in vacuo to afford the title compound (310 mg, 97%) as yellow oil.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 18 h
  2. customThe reaction was partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution
  3. washThe organic layer was washed with brine
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ef37130df99e4effbed25500bbafa5df
Source dataset
uspto-grants-2015_09
Patent number
US09133185B2

Reaction notes

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