Water → HCID 58710608, compound

HRID 646712Notes

Reaction equation

HRID 646712 reaction equation
O=[C:2]1[NH:7][C:6]2[CH:8]=[C:9]([C:12]#[N:13])[CH:10]=[CH:11][C:5]=2[O:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)(=O)C>[O:4]1[C:5]2[CH:11]=[CH:10][C:9]([CH2:12][NH2:13])=[CH:8][C:6]=2[NH:7][CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 106548133-Oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 58710608HCID 58710608, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3,4-Dihydro-2H-1,4-benzoxazine-6-ylmethyl)amine: a solution of 3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-carbonitrile (1.3 g ) in anhydrous TBF (20 mL) was slowly added to a stirred and ice -cooled solution of lithium aluminum hydride (30 mL, 1 M solution in THF). With continued cooling water (5 mmol) and sodium hydroxide (5 mL, 20% solution), water (20 mL) and ethyl acetate (30 mL) were added in succession. The organic solution was decanted from the white residue. The residue was washed twice with ether, all the organic solution were combined then dried over anhydrous sodium sulfate. Filtration and concentration followed by drying in vacuo afforded 3,4-dihydro-2H-1,4-benzoxazine-6-ylmethylamine (0.78 g,): 1H NMR (400 MHz; DMSO-D6): 6.52 (d, 1H); 6.49 (s, 1H); 6.37 (d, 1H); 5.6 (br s, NH); 4.05 (t, 2H); 3.4 (m, 2H).

Workup

  1. additionwere added in succession
  2. customThe organic solution was decanted from the white residue
  3. washThe residue was washed twice with ether, all the organic solution
  4. dry with materialwere combined then dried over anhydrous sodium sulfate
  5. filtrationFiltration and concentration
  6. customby drying in vacuo

Sources & evidence

ORD record
ord-f619e409009c45c5a33bb7c776b6313d
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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