Dimethylformamide → Sch 37224

HRID 330591

反応式

HRID 330591 の反応式
[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

参加物

5

反応物 4

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

生成物 1

HCID 54680204Sch 37224収率 60%

反応条件

温度
0 °C

実験手順

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 (14.54 M) 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.

後処理

  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

出典と根拠

ORDレコード
ord-ee98899de7be4328bac531e9cd9c5445
出典データセット
uspto-grants-1990_01
特許番号
US04897487

関連ノート

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