Ammonium Acetate → 4-Aminochroman-7-carbonitrile

HRID 896243Notes

Reaction equation

HRID 896243 reaction equation
[C:1]([C:3]1[CH:12]=[C:11]2[C:6]([C:7](=O)[CH2:8][CH2:9][O:10]2)=[CH:5][CH:4]=1)#[N:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:20].[Na+]>>[C:1]([C:3]1[CH:12]=[C:11]2[C:6]([CH:7]([NH2:20])[CH2:8][CH2:9][O:10]2)=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 223499736-Cyano-4-chromanone

Product 1

HCID 223499724-Aminochroman-7-carbonitrileYield 60.6%

Procedure

A dry, 200 mL round bottom flask was charged with 0.85 g (4.83 mmol) of 7-(cyano)-4-chromanone, 3.72 g (48.30 mmol) of ammonium acetate, and 0.91 g (14.45 mmol) of sodium cyanoborohydride. The flask was then purged with argon, and 30 mL of dry methanol was added by syringe. The solution was stirred at room temp for 48 hours. Concentrated HCl was slowly added dropwise until pH<2 was reached. The methanol was then evaporated by rotovap, and 30 mL of water was added to the suspension, which was then washed 3 times with ethyl acetate. The pH was then brought to >10 by adding sodium hydroxide pellets to the stirring aqueous mixture. Saturated sodium chloride was added, and the mixture was then extracted several times with ether and ethyl acetate. The combined organic phase was dried over magnesium sulfate, filtered and evaporated to give 0.51 g (60%) of the desired 7-(cyano)-4-chromanylamine as a pale yellow oil.

Workup

  1. customThe flask was then purged with argon, and 30 mL of dry methanol
  2. additionwas added by syringe
  3. additionConcentrated HCl was slowly added dropwise until pH<2
  4. customThe methanol was then evaporated by rotovap, and 30 mL of water
  5. additionwas added to the suspension, which
  6. washwas then washed 3 times with ethyl acetate
  7. additionby adding sodium hydroxide pellets to the stirring aqueous mixture
  8. additionSaturated sodium chloride was added
  9. extractionthe mixture was then extracted several times with ether and ethyl acetate
  10. dry with materialThe combined organic phase was dried over magnesium sulfate
  11. filtrationfiltered
  12. customevaporated

Sources & evidence

ORD record
ord-b62b4bb4076841c78d1782372e41a67c
Source dataset
uspto-grants-2005_07
Patent number
US06919347B2

Reaction notes

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