(4E)-N-Methoxy-6-methyl-3,4-dihydro-2H-1-benzopyran-4-imine → 6-Methylchroman-4-amine

HRID 1803755Notes

Reaction equation

HRID 1803755 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.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

5

Reactant 1

HCID 86605441(4E)-N-Methoxy-6-methyl-3,4-dihydro-2H-1-benzopyran-4-imine

Product 1

HCID 162444176-Methylchroman-4-amine

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

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

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe residue dissolved in diethyl ether which
  4. washwas washed sequentially with water and saturated aqueous sodium bicarbonate
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d8f1a0860872431fb0291d0b40382beb
Source dataset
uspto-grants-2013_01
Patent number
US08350083B2

Reaction notes

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