Triethyl orthoacetate → HCID 12669654, compound

HRID 1448565Notes

Reaction equation

HRID 1448565 reaction equation
[C:1]([C:3](=[C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([OH:16])=[CH:8]1)[C:4]([NH2:6])=[O:5])#[N:2].[CH2:17](OC(OCC)(OCC)C)[CH3:18]>CN(C)C=O>[CH3:17][C:18]1[NH:6][C:4](=[O:5])[C:3]([C:1]#[N:2])=[C:7]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:9](=[O:16])[C:8]=12

Participants

4

Reactant 2

HCID 66221Triethyl orthoacetateHCID 70610994HCID 70610994, compound

Product 1

HCID 12669654HCID 12669654, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1 part of 2-cyano-2-(3-hydroxy-1H-inden-1-ylidene)acetamide, 1 part of 1,1,1-triethoxyethane, and approximately 6 parts of N,N-dimethylformamide is heated at 90°-95° under reflux for 2 hours, whereupon the precipitate which forms is filtered out, washed with ethyl acetate, and dried in vacuo. Crystallization from ethyl acetate affords needles of 3,9-dihydro-1-methyl-3,9-dioxo-2H-indeno[2,1-c]pyridine-4-carbonitrile melting above 300°. The product has the formula ##STR7##

Workup

  1. temperatureis heated at 90°-95°
  2. temperatureunder reflux for 2 hours, whereupon the precipitate which
  3. filtrationforms is filtered out
  4. washwashed with ethyl acetate
  5. customdried in vacuo
  6. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-895775af6c7f4b54bda386ff82ad6120
Source dataset
uspto-grants-1979_12
Patent number
US04180666

Reaction notes

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