Ammonia → 7-tert-Butyl-chroman-4-ylamine

HRID 1158787Notes

Reaction equation

HRID 1158787 reaction equation
CO[N:3]=[C:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:11][CH:12]=2)[O:7][CH2:6][CH2:5]1.N>CO.[Pd]>[C:14]([C:10]1[CH:9]=[C:8]2[C:13]([CH:4]([NH2:3])[CH2:5][CH2:6][O:7]2)=[CH:12][CH:11]=1)([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 866054407-tert-Butyl-chroman-4-one O-methyl-oxime

Product 1

HCID 672368437-tert-Butyl-chroman-4-ylamineYield 104%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The product of Example 1B (1.53g) was taken into a solution of 20% ammonia in methanol, and hydrogenated for 4 hours at 60 psi at 50° C. in the presence of 1.55 g of 10% palladium on carbon as catalyst. The reaction mixture was filtered to remove catalyst, and the solvent removed under reduced pressure to give 1.40 g of the title compound (93% for two steps). 1H NMR(300 MHz, CDCl3) δ 7.25 (d, 1H, J=6.8 Hz), 6.96 (dd, 1H, J=2.0 and 8.1 Hz), 6.85 (d, 1H, J=2.0 Hz), 4.18-4.32 (m, 2H), 4.04 (t, 1H), 2.11-2.21 (m, 1H), 1.80-1.90 (m, 1H), 1.29 (s, 9H). MS (DCI) m/e 206 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove catalyst
  3. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-58882c344cb448919ef36db65717832c
Source dataset
uspto-grants-2010_10
Patent number
US07812019B2

Reaction notes

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