Ammonia → 6-Methylchroman-4-amine

HRID 1158796Notes

Reaction equation

HRID 1158796 reaction equation
CO[N:3]=[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH3:14])[CH:12]=2)[O:7][CH2:6][CH2:5]1.N.[H][H]>CO.[Ni]>[CH3:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[O:7][CH2:6][CH2:5][CH:4]2[NH2:3]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 86605441(4E)-N-Methoxy-6-methyl-3,4-dihydro-2H-1-benzopyran-4-imineHCID 178418361HCID 178418361, compound

Product 1

HCID 162444176-Methylchroman-4-amineYield 61.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of the product of Example 7A (4.24 g) in 50 mL of a mixture of 20% ammonia in methanol was treated with 40 g Raney Nickel under 60 psi hydrogen for 4 hours at ambient temperature. The reaction mixture was filtered, and the solvent evaporated under reduced pressure. The residue was taken in diethyl ether, washed sequentially with water and saturated aqueous sodium bicarbonate, dried with magnesium sulfate, filtered and concentrated to give 2.22 g of the title compound. H NMR (300 MHz, CDCl3) δ 7.11 (s, 1H), 6.95 (d, 1H, J=8.5 Hz), 6.71 (d, 1H, J=8.5 Hz), 4.22 (m, 2H), 4.01 (m, 1H), 2.27 (s, 3H), 2.10-2.21 (m, 1H), 1.78-1.88 (m, 1H). MS (DCI) m/e 164 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent evaporated under reduced pressure
  3. washwashed sequentially with water and saturated aqueous sodium bicarbonate
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-53be66ec0f4e4fdf8c1e6452e5f7c960
Source dataset
uspto-grants-2010_10
Patent number
US07812019B2

Reaction notes

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