Hydrochloric Acid → HCID 19095955, compound

HRID 486769Notes

Reaction equation

HRID 486769 reaction equation
[OH:1][C:2]1[C:7]2=[CH:8][C:9]3[C:14]([N:6]2[CH2:5][CH2:4][C:3]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=[CH:11][CH:10]=3.[C:20]([O:24][CH3:25])(=[O:23])[CH:21]=[CH2:22].CN(C)C(N(C)C)=N.Cl>C(#N)C.O>[CH2:18]([O:17][C:15]([C:3]1([CH2:22][CH2:21][C:20]([O:24][CH3:25])=[O:23])[CH2:4][CH2:5][N:6]2[C:14]3[C:9]([CH:8]=[C:7]2[C:2]1=[O:1])=[CH:10][CH:11]=[CH:12][CH:13]=3)=[O:16])[CH3:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7294Methyl AcrylateHCID 664601,1,3,3-TetramethylguanidineHCID 54678585HCID 54678585, compound

Product 1

HCID 19095955HCID 19095955, compoundYield 94.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 5 g of ethyl 6,7-dihydro-9-hydroxypyrido[1,2-a]indole-8-carboxylate. 1.85 g of methyl acrylate and 250 mg of 1,1,3,3-tetramethylguanidine was dissolved in 250 ml of acetonitrile and the solution was stirred overnight, poured into 500 ml of water containing 20 ml of 2M hydrochloric acid and extracted with diethyl ether. The ethereal extracts were washed with water, dried and concentrated. There were obtained 6.33 g of methyl 8-(ethoxycarbonyl)-6,7,8,9-tetrahydro-9-oxopyrido[1,2-a]indole-8-propionate.

Workup

  1. extractionextracted with diethyl ether
  2. washThe ethereal extracts were washed with water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5bf2d5690c324cf4bdc00e1d4b877aa1
Source dataset
uspto-grants-1994_03
Patent number
US05292747

Reaction notes

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