3,4-dihydro-2,5-dimethyl-8-nitro-2H-1-benzopyran → 8-amino-3,4-dihydro-2,5-dimethyl-2H-1-benzopyran

HRID 637629Notes

Reaction equation

HRID 637629 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][C:5]2[C:8]([CH3:15])=[CH:9][CH:10]=[C:11]([N+:12]([O-])=O)[C:4]=2[O:3]1.[H][H]>[Ni].C1COCC1>[NH2:12][C:11]1[C:4]2[O:3][CH:2]([CH3:1])[CH2:7][CH2:6][C:5]=2[C:8]([CH3:15])=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 135602963,4-dihydro-2,5-dimethyl-8-nitro-2H-1-benzopyranHCID 178418361HCID 178418361, compound

Product 1

HCID 135602978-amino-3,4-dihydro-2,5-dimethyl-2H-1-benzopyran

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 27 g of 1D, 200 ml of THF and 2 g of activated Raney nickel catalyst was treated with hydrogen (40 psig) in a Parr shaker for 3 hours. The resulting mixture was dried (MgSO4), filtered and concentrated to dryness, to give 8-amino-3,4-dihydro-2,5-dimethyl-2H-1-benzopyran (1E), as an amber syrup.

Workup

  1. dry with materialThe resulting mixture was dried (MgSO4)
  2. filtrationfiltered
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-2462054442c0426eb55e986976b6dd42
Source dataset
uspto-grants-1985_12
Patent number
US04558040

Reaction notes

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