Acetic Acid → HCID 13885833, compound

HRID 653156Notes

Reaction equation

HRID 653156 reaction equation
CC(C)([O-])C.[K+].C[O:8][C:9](=O)[C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=1[N:18]([CH2:25][C:26]#[N:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(O)(=O)C>O1CCCC1>[OH:8][C:9]1[C:10]2[C:11](=[CH:12][CH:13]=[C:14]([O:16][CH3:17])[CH:15]=2)[N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:25]=1[C:26]#[N:27]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 13885835HCID 13885835, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 13885833HCID 13885833, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 8.4 g (0.075 mole) of potassium tert.-butoxide in 200 ml of tetrahydrofuran (under a nitrogen atmosphere) was stirred and cooled in an ice bath. A solution of 13.7 g (0.046 mole) of 2-[(cyanomethyl)phenylamino]-5-methoxybenzoic acid methyl ester in 150 ml of tetrahydrofuran was added over two hours, the ice bath was removed, and the new mixture was stirred for an additional 42 hours. The total reaction mixture was added to 1.1 kg of ice/water and acidified with 12.0 ml of glacial acetic acid to precipitate the crude product. The solid was filtered, washed with water, and recrystallized from aqueous methanol to yield 10.3 g (84% yield) of the nitrile product. A sample recrystallized again as above was analytically pure, mp 182° C.-dec.

Workup

  1. temperaturecooled in an ice bath
  2. customthe ice bath was removed
  3. stirringthe new mixture was stirred for an additional 42 hours
  4. customThe total reaction mixture
  5. customto precipitate the crude product
  6. filtrationThe solid was filtered
  7. washwashed with water
  8. customrecrystallized from aqueous methanol

Sources & evidence

ORD record
ord-d495a912f4f742e5bb45b945ad93e098
Source dataset
uspto-grants-1987_06
Patent number
US04675332

Reaction notes

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