Hydrochloric Acid → 4-Amino-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran

HRID 344772Notes

Reaction equation

HRID 344772 reaction equation
[N:1]([CH:4]1[C:9]2[CH:10]=[C:11]([C:14]#[N:15])[CH:12]=[CH:13][C:8]=2[O:7][C:6]([CH3:17])([CH3:16])[CH2:5]1)=[N+]=[N-].Cl>CC(C)=O.O.[Zn]>[NH2:1][CH:4]1[C:9]2[CH:10]=[C:11]([C:14]#[N:15])[CH:12]=[CH:13][C:8]=2[O:7][C:6]([CH3:17])([CH3:16])[CH2:5]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 101051694-azido-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran

Product 1

HCID 118201634-Amino-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyranYield 84.6%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of 4-azido-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran (0.92g) in acetone (20 ml) was added concentrated hydrochloric acid (3 ml) and zinc dust (0.6g) in portions, with vigorous stirring. After 15 min the reaction was diluted with water, filtered and the filtrate extracted with ethyl acetate. The aqueous phase was made basic with 10% (w/v) aqueous sodium hydroxide solution and further extracted with ethyl acetate. The combined organic phase was dried over anhydrous sodium sulphate, filtered and the solvent evaporated in vacuo to give the title compound (0.69g).

Workup

  1. filtrationfiltered
  2. extractionthe filtrate extracted with ethyl acetate
  3. extractionfurther extracted with ethyl acetate
  4. dry with materialThe combined organic phase was dried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-af81beb2bb7d4821afe00abbc25524c9
Source dataset
uspto-grants-1991_10
Patent number
US05053427

Reaction notes

Loading…