O-Methylhydroxylamine hydrochloride → (4E)-N-Methoxy-6-methyl-3,4-dihydro-2H-1-benzopyran-4-imine

HRID 1803754Notes

Reaction equation

HRID 1803754 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH2:6][C:5]2=O.Cl.[O:14]([NH2:16])[CH3:15]>N1C=CC=CC=1>[CH3:15][O:14][N:16]=[C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([CH3:1])[CH:3]=2)[O:8][CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 5843546-Methyl-4-chromanone

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

6-Methylchroman-4-one (Aldrich, 3.24 g, 20 mmol) was dissolved in pyridine (15 mL). Methoxyl amine hydrochloride (1.84 g, 22 mmol) was added and the mixture stirred for 16 hours at ambient temperature. The pyridine was removed under reduced pressure, and the residue was added to water and diethyl ether. The aqueous layer was extracted with diethyl ether, and the combined organic layers washed with 1N sodium hydroxide and 1N hydrochloric acid and then dried with magnesium sulfate and filtered. The solvent was removed under reduced pressure to afford the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 2.28 (s, 3H), 2.88 (t, J=6.27 Hz, 2H), 3.98 (s, 3H), 4.17 (t, J=6.27 Hz, 2H), 6.78 (d, J=8.48 Hz, 1H), 7.05 (dd, J=8.48, 2.03 Hz, 1H), 7.70 (d, J=2.03 Hz, 1H). MS (DCI) m/z 192.02 (M+H)+.

Workup

  1. customThe pyridine was removed under reduced pressure
  2. additionthe residue was added to water and diethyl ether
  3. extractionThe aqueous layer was extracted with diethyl ether
  4. washthe combined organic layers washed with 1N sodium hydroxide and 1N hydrochloric acid
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1ecb5b30cca24fbb8784cf81fb8261bc
Source dataset
uspto-grants-2013_01
Patent number
US08350083B2

Reaction notes

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