Potassium Carbonate → HCID 68139207, compound

HRID 1729993Notes

Reaction equation

HRID 1729993 reaction equation
[CH3:1][O:2][C:3](=[O:6])[CH2:4]Br.[CH3:7][C:8]1[C:9]2[C:14]([CH:15]3[C:20]=1[CH2:19][CH2:18][NH:17][CH2:16]3)=[CH:13][CH:12]=[CH:11][CH:10]=2.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][O:2][C:3](=[O:6])[CH2:4][N:17]1[CH2:18][CH2:19][C:20]2=[C:8]([CH3:7])[C:9]3[C:14]([CH:15]2[CH2:16]1)=[CH:13][CH:12]=[CH:11][CH:10]=3

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 214987881,3,4,9b-tetrahydro-5-methyl-2H-indeno[1,2-c]pyridine

Product 1

HCID 68139207HCID 68139207, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 15.3 g of bromoacetic acid methyl ester in 50 cc of dimethyl formamide is added dropwise at 60° while stirring to a mixture of 18.5 g of 1,3,4,9b-tetrahydro-5-methyl-2H-indeno[1,2-c]pyridine and 41.4 g of potassium carbonate in 200 cc of dimethyl formamide. The reaction mixture is allowed to react at 60° for 1 hour, is poured on ice water and is extracted thrice with chloroform. The extracts are dried and completely concentrated by evaporation, the residue is dissolved in 50 cc of methanol, and the calculated amount of hydrochloric acid in ethanol is added. After the addition of ether, 1,3,4,9 b-tetrahydro-5-methyl-2H-indeno [1,2-c]pyridine-2-acetic acid methyl ester crystallizes as hydrochloride and is recrystallized twice from ethanol for further purification. The hydrochloride has a M.P. of 184°-185°.

Workup

  1. customto react at 60° for 1 hour
  2. additionis poured on ice water
  3. extractionis extracted thrice with chloroform
  4. customThe extracts are dried
  5. concentrationcompletely concentrated by evaporation
  6. dissolutionthe residue is dissolved in 50 cc of methanol
  7. additionthe calculated amount of hydrochloric acid in ethanol is added
  8. additionAfter the addition of ether, 1,3,4,9 b-tetrahydro-5-methyl-2H-indeno [1,2-c]pyridine-2-acetic acid methyl ester
  9. customcrystallizes as hydrochloride
  10. customis recrystallized twice from ethanol for further purification

Sources & evidence

ORD record
ord-2f012fb97c084138add6544dcb5958f2
Source dataset
uspto-grants-1976_11
Patent number
US03991066

Reaction notes

Loading…