Sodium Hydroxide → 2,2-Dimethyl-2H-chromen-6-amine

HRID 373679Notes

Reaction equation

HRID 373679 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:14])([CH3:13])[CH:10]=[CH:9][C:8]=2[CH:15]=1)([O-])=O.Cl[Sn]Cl.[OH-].[Na+]>C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:13])([CH3:14])[CH:10]=[CH:9][C:8]=2[CH:15]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 103756666-Nitro-2,2-dimethylchromene

Product 1

HCID 100808812,2-Dimethyl-2H-chromen-6-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6-nitro-2,2-dimethyl-2H-benzopyran (prepared as described in Evans et al., J. Med. Chem.) (4.65 g, 22.66 mmoles) and SnCl2. 2H2O (25.57 g, 0.11 mole) in ethanol (46.5 ml) was heated at reflux for 45 minutes. The reaction mixture was poured onto ice/H2O (180 g), made basic (pH 10-11) with 50% sodium hydroxide solution, and extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried over sodium sulfate, and evaporated in vacuo to obtain 3.88 g of the title A compound as a brown oil.

Workup

  1. temperatureat reflux for 45 minutes
  2. additionThe reaction mixture was poured onto ice/H2O (180 g)
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-f3355ff9e0934114a75c1934d17a4266
Source dataset
uspto-grants-1992_11
Patent number
US05164509

Reaction notes

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