Sodium hydride → 2-(2-oxopyrrolidin-1-yl)-N-(3-methyl-5,6,7,8-tetrahydrothieno[2,3-b]quinolin-4-yl)acetamide

HRID 1816230Notes

Reaction equation

HRID 1816230 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:13]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=2[N:7]=[C:6]2[S:14][CH:15]=[C:16]([CH3:17])[C:5]=12.[O:18]=[C:19]1[CH2:23][CH2:22][CH2:21][N:20]1[CH2:24][C:25](OC)=[O:26].[Cl-].[NH4+]>C(N1CCCC1=O)C>[O:18]=[C:19]1[CH2:23][CH2:22][CH2:21][N:20]1[CH2:24][C:25]([NH:3][C:4]1[C:13]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=2[N:7]=[C:6]2[S:14][CH:15]=[C:16]([CH3:17])[C:5]=12)=[O:26]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 108835Methyl 2-oxo-1-pyrrolidineacetateHCID 152251184-Amino-3-methyl-5,6,7,8-tetrahydrothieno[2,3-b]quinoline

Product 1

HCID 153850712-(2-oxopyrrolidin-1-yl)-N-(3-methyl-5,6,7,8-tetrahydrothieno[2,3-b]quinolin-4-yl)acetamideYield 83.5%

Reagents, catalysts & solvents 1

HCID 17595N-ethyl-2-pyrrolidoneSolvent

Procedure

Into a suspension of 1.26 g of sodium hydride (60% content) in 15 ml of N-ethylpyrrolidone, was added 3.28 g of 4-amino-3-methyl-5,6,7,8-tetrahydrothieno[2,3-b]quinoline at room temperature. The mixture was heated to 50.degree. C. and stirred for 40 minutes. Thereafter, 4.72 g of methyl 2-oxo-1-pyrrolidine acetate was added dropwise to the mixture at 50.degree. C. over a period of 30 minutes. After the stirring at 50.degree. C. for 20 minutes, the mixture was cooled to 15.degree. C. and poured into 130 ml aqueous solution containing 13.5 g of ammonium chloride. After extraction of the solution with 100 ml of chloroform, the extract was dried over anhydrous sodium sulfate, followed by evaporation to dryness. The resultant product was added with ethyl acetate, pulverized and filtered. The crude crystals were recrystallized from chloroform-ethyl acetate to obtain 4.31 g of the titled compound having the melting point of 244.degree. to 246.degree. C.

Workup

  1. temperatureThe mixture was heated to 50.degree
  2. waitover a period of 30 minutes
  3. waitfor 20 minutes
  4. temperaturethe mixture was cooled to 15.degree
  5. extractionAfter extraction of the solution with 100 ml of chloroform
  6. dry with materialthe extract was dried over anhydrous sodium sulfate
  7. customfollowed by evaporation to dryness
  8. additionThe resultant product was added with ethyl acetate
  9. filtrationfiltered
  10. customThe crude crystals were recrystallized from chloroform-ethyl acetate

Sources & evidence

ORD record
ord-d6a88223d27d4a089f4e7d1ba1a8e913
Source dataset
uspto-grants-2005_04
Patent number
US06884805B2

Reaction notes

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