Aluminium lithium hydride → HCID 68554248, compound

HRID 2382117Notes

Reaction equation

HRID 2382117 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[CH:9]=[CH:10][C:11]2[O:16][CH2:15][CH2:14][N:13]([N:17]=O)[C:12]=2[CH:19]=1>C1COCC1>[F:7][C:8]1[CH:9]=[CH:10][C:11]2[O:16][CH2:15][CH2:14][N:13]([NH2:17])[C:12]=2[CH:19]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 866393826-Fluoro-4-nitroso-3,4-dihydro-2H-benzo[1,4]oxazine

Product 1

HCID 68554248HCID 68554248, compoundYield 0.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

LiAlH4 in THF (1 M, 6.58 mL) is added to a solution of 6-fluoro-4-nitroso-3,4-dihydro-2H-benzo[1,4]oxazine (0.8 g) in THF (10 mL) at 00 C. and then stirred at rt overnight. The reaction mixture is quenched with a few drops of water followed by addition of EtOAc (10 mL). The solid is filtered off and washed with EtOAc (15 mL). The filtrate is concentrated in vacuo and the residue is purified by silica gel column chromatography eluting with 15% EtOAc in heptane to afford 6-fluoro-2,3-dihydro-benzo[1,4]oxazin-4-ylamine (0.44 mg).

Workup

  1. customThe reaction mixture is quenched with a few drops of water
  2. additionfollowed by addition of EtOAc (10 mL)
  3. filtrationThe solid is filtered off
  4. washwashed with EtOAc (15 mL)
  5. concentrationThe filtrate is concentrated in vacuo
  6. customthe residue is purified by silica gel column chromatography
  7. washeluting with 15% EtOAc in heptane

Sources & evidence

ORD record
ord-5b9fab7643cb4a659da22f22c61899dd
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

Loading…