HCID 20161193, compound → HCID 20161200, compound

HRID 247017Notes

Reaction equation

HRID 247017 reaction equation
O[C:2]1([C:15]#[N:16])[CH2:10][C:9]2[C:4](=[CH:5][C:6]([O:13][CH3:14])=[C:7]([O:11][CH3:12])[CH:8]=2)[CH2:3]1>Cl>[CH3:14][O:13][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][C:7]=1[O:11][CH3:12])[CH2:10][C:2]([C:15]#[N:16])=[CH:3]2

Participants

3

Reactant 1

HCID 20161193HCID 20161193, compound

Product 1

HCID 20161200HCID 20161200, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
75 °C

Procedure

The crude alcohol (17.1 g) was suspended in hydrochloric acid (5M, 170 ml) and the mixture was stirred and heated to 75° C. After 30 min. the dark solution was cooled in an ice-bath and the resultant green solid was filtered off and dried at 60° C. The product was dissolved in dichloromethane and the solution was passed through a column of coarse silica (0.2-0.5 mm, Merck, 80 g). The appropriate fractions were combined and evaporated to dryness to give 5,6-dimethoxy-1H-indene-2-carbonitrile (12.6 g), m.p. 140°-141° C.

Workup

  1. temperatureAfter 30 min. the dark solution was cooled in an ice-bath
  2. filtrationthe resultant green solid was filtered off
  3. customdried at 60° C
  4. dissolutionThe product was dissolved in dichloromethane
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-b2e11faffd634216adb7d3266e55c54e
Source dataset
uspto-grants-1987_11
Patent number
US04705782

Reaction notes

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