Dimethylformamide → Sch 37224

HRID 1646663Notes

Reaction equation

HRID 1646663 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH3:7])[CH:5]=[O:6].C(O[C:11](=[O:18])[CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)C.C1(C)[C:20](C)=[CH:21][CH:22]=[CH:23][CH:24]=1>>[OH:18][C:11]1[C:17]2[C:3](=[N:13][CH:14]=[CH:15][CH:16]=2)[N:4]([C:7]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:5](=[O:6])[C:12]=1[N:13]1[CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7237O-XyleneHCID 24758Sodium hydride2×HCID 2109961-Pyrrolidineacetic acid, ethyl ester2×

Product 1

HCID 54680204Sch 37224Yield 60%

Conditions

Temperature
0 °C

Procedure

To a solution of 1.5 g (6.5 mM) 2-anilinonicotinic acid, methylester, in dry xylenes at room temperature is added 0.69 g (14.54M) of sodium hydride (NaH) (50 percent (%) oil emulsion) followed by addition of a small amount of N,N-dimethylformamide (DMF). The reaction mixture is heated to a temperature ranging between 85-95 degrees Centigrade (° C) and 1.05 milliliters (mL) (6.5 mM) of ethyl-1-pyrrolidineacetate in xylene is slowly added over a period of 10 minutes. The reaction mixture is heated for 1 to 3 hours prior to the addition of aliquots of 0.32 g NaH followed by 1.05 mL of ethyl-1-pyrrolidineacetate as described above (total 3 aliquots). Following addition of the aliquots, the reaction mixture is cooled to 0° C., quenched with a slow addition of glacial acetic acid, and then water is added. The product is filtered and washed with water, acetone, methylene chloride, and acetone. The solid then obtained is dried in vacuo to give 1.20 g (60% yield) of title compound, a white solid.

Workup

  1. temperatureThe reaction mixture is heated to a temperature
  2. customranging between 85-95 degrees Centigrade
  3. additionis slowly added over a period of 10 minutes
  4. temperatureThe reaction mixture is heated for 1 to 3 hours
  5. additionaddition of the aliquots
  6. customquenched with a slow addition of glacial acetic acid
  7. additionwater is added
  8. filtrationThe product is filtered
  9. washwashed with water, acetone, methylene chloride, and acetone
  10. customThe solid then obtained
  11. customis dried in vacuo

Sources & evidence

ORD record
ord-22f288b4614d49c98eff49971e5c1bb5
Source dataset
uspto-grants-1993_01
Patent number
US05180823

Reaction notes

Loading…