Acetic Acid → HCID 783358, compound

HRID 1521737Notes

Reaction equation

HRID 1521737 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+]>O1CCCC1.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 tetrahydrofuran (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) and the reaction is stirred overnight. The reaction is poured into a saturated aqueous Na2CO3 solution and extracted with ethyl acetate. The combined extracts are washed with H2O, brine, dried (Na2SO4) and concentrated to afford a clear oil. The residue is taken up in 1N aqueous HCl and removed insoluble material 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 H2O, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customto afford a clear oil
  6. customremoved insoluble material
  7. filtrationby filtration
  8. custompartitioned into ethyl acetate
  9. dry with materialThe organic layer is dried (Na2SO4)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-25b175da397a458e85cecd2c1cf6cdd9
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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