Water → HCID 118308726, compound

HRID 923475Notes

Reaction equation

HRID 923475 reaction equation
[CH3:1][C:2]1([CH3:21])[O:7][CH2:6][C:5]([C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=2)[C:14]([O:16][CH3:17])=[O:15])([N+:8]([O-])=O)[CH2:4][O:3]1.O>C(O)C.C1COCC1.[Ni]>[NH2:8][C:5]1([C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=2)[C:14]([O:16][CH3:17])=[O:15])[CH2:6][O:7][C:2]([CH3:1])([CH3:21])[O:3][CH2:4]1

Participants

6

Reactant 2

HCID 962WaterHCID 118308683HCID 118308683, compound

Product 1

HCID 118308726HCID 118308726, compoundYield 106.7%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere, to a solution of 2.18 g of methyl 3-(2,2-dimethyl-5-nitro-1,3-dioxan-5-yl)benzoate in 26 ml of ethanol and 7 ml of THF was added a suspension of Raney nickel (manufactured by Aldrich, 1.2 ml of a suspension was washed with water and ethanol) in 5 ml of ethanol, followed by stirring at room temperature for 7 hours under a hydrogen atmosphere of 4 atm. The reaction mixture was filtered over Celite and the liquid was concentrated under reduced pressure. To a solution of the obtained residue in 26 ml of ethanol and 7 ml of THF was added a suspension of Raney nickel (manufactured by Aldrich, 1.2 ml of a suspension was washed with water and ethanol) in 5 ml of ethanol under an argon atmosphere, followed by stirring at room temperature for 16 hours under a hydrogen atmosphere of 4 atm. The reaction mixture was filtered over Celite and the filtrate was concentrated under reduced pressure to obtain 2.09 g of methyl 3-(5-amino-2,2-dimethyl-1,3-dioxan-5-yl)benzoate.

Workup

  1. filtrationThe reaction mixture was filtered over Celite
  2. concentrationthe liquid was concentrated under reduced pressure
  3. additionTo a solution of the obtained residue in 26 ml of ethanol and 7 ml of THF was added
  4. additiona suspension of Raney nickel (manufactured by Aldrich, 1.2 ml of a suspension was washed with water and ethanol) in 5 ml of ethanol under an argon atmosphere
  5. stirringby stirring at room temperature for 16 hours under a hydrogen atmosphere of 4 atm
  6. filtrationThe reaction mixture was filtered over Celite
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-abdcddf314bd4a7693ea4be4933b3136
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

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