Acetic Acid → HCID 783358, compound

HRID 1748338Notes

Reaction equation

HRID 1748338 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([N+:16]([O-:18])=[O:17])=[C:12]([CH:15]=1)[CH:13]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CC(O)=O.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.Cl>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([N+:16]([O-:18])=[O:17])=[C:12]([CH:15]=1)[CH2:13][N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 8083MorpholineHCID 10340Sodium CarbonateHCID 811235-Chloro-2-nitrobenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 783358HCID 783358, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of morpholine (2.8 mL, 32.3 mmol) in THF (100 mL) is added 5-chloro-2-nitrobenzaldehyde (5 g, 26.9 mmol) followed by sodium triacetoxyborohydride (11.4 g, 53.9 mmol) and HOAc (3.2 mL, 53.9 mmol). The reaction is stirred for 16 h. The reaction is poured into a saturated aqueous Na2CO3 solution and extracted with ethyl acetate. The combined extracts are washed with water, brine, dried (Na2SO4) and concentrated to afford a clear oil. The residue is taken up in 1N aqueous HCl and the insoluble material is removed by filtration. The filtrate is neutralized with 2M aqueous K2CO3 and partitioned into ethyl acetate. The organic layer is dried (Na2SO4) and concentrated to afford the title compound (5.1 g, 74%) as an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts are washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customto afford a clear oil
  6. customthe insoluble material is removed by filtration
  7. custompartitioned into ethyl acetate
  8. dry with materialThe organic layer is dried (Na2SO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-c7af3bbc14ea429783c02e83cd240c1a
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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