Ammonia → 6-Methylchroman-4-amine

HRID 2092156Notes

Reaction equation

HRID 2092156 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 Nickle 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. 1H 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-0a4688604a4f435883c93ab7c450127d
Source dataset
uspto-grants-2013_05
Patent number
US08440691B2

Reaction notes

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