3,4-dihydro-2H-1,4-benzoxazine-2-carbonitrile → 1-(3,4-Dihydro-2H-1,4-benzoxazin-2-yl)methanamine

HRID 1483030Notes

Reaction equation

HRID 1483030 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][CH2:3][CH:2]1[C:11]#[N:12].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][CH2:3][CH:2]1[CH2:11][NH2:12]

Participants

4

Reactant 2

HCID 27955043,4-dihydro-2H-1,4-benzoxazine-2-carbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 105589581-(3,4-Dihydro-2H-1,4-benzoxazin-2-yl)methanamineYield 63.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add 3,4-dihydro-2H-1,4-benzoxazine-2-carbonitrile (600 mg, 3.75 mmol) to THF (20 mL) and then slowly add lithium aluminum hydride (1.0 M in THF; 1 mL, 1.0 mmol). Stir the mixture at ambient temperature for 30 minutes. Add H2O (1 mL) to quench the reaction; filter; and wash the filter cake with EtOAc. Dry the filtrate over Na2SO4; filter; and concentrate the filtrate under reduced pressure to afford a residue. Purify the resulting compound via flash column chromatography using a gradient of 20-50% of MeOH in DCM. Combine the desired fractions and remove the solvents under reduced pressure to provide the title compound as a white solid (390 mg, 63.1%). MS (m/z): 165 (M+1).

Workup

  1. customAdd H2O (1 mL) to quench
  2. customthe reaction
  3. filtrationfilter
  4. washand wash the filter cake with EtOAc
  5. dry with materialDry the filtrate over Na2SO4
  6. filtrationfilter
  7. concentrationand concentrate the filtrate under reduced pressure
  8. customto afford a residue
  9. customPurify the resulting compound via flash column chromatography
  10. customremove the solvents under reduced pressure

Sources & evidence

ORD record
ord-b031708bf51e4e94abbe97956ca46d55
Source dataset
uspto-grants-2016_08
Patent number
US09416138B2

Reaction notes

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