Ammonium formate → HCID 53328723, compound

HRID 1190885Notes

Reaction equation

HRID 1190885 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([CH2:11][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[C:3]=1[N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.C([O-])=O.[NH4+]>CCO.[Pd]>[CH3:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([CH2:11][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[C:3]=1[N:17]1[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1)[NH2:8]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 53328350HCID 53328350, compound

Product 1

HCID 53328723HCID 53328723, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-[2-Methyl-4-nitro-6-(pyrrolidin-1-ylmethyl)phenyl]morpholine (62 mg, 0.20 mmol) was hydrogenated using ammonium formate (128 mg, 2.00 mmol) and Pd/C (10% Pd, 21 mg, 0.02 mmol) in 2 mL of EtOH. The mixture was stirred overnight at room temperature and then filtered through a celite pad. The filtrate was evaporated and the residue was dissolved in DCM and washed with a saturated aqueous solution of Na2CO3. The aqueous layer was extracted with DCM. The combined organic layers were dried over Na2SO4, filtered and evaporated to yield expected compound as a pale yellow oil (55 mg, 99% yield); m/z (ESI) 276.3 [M+H]+.

Workup

  1. filtrationfiltered through a celite pad
  2. customThe filtrate was evaporated
  3. dissolutionthe residue was dissolved in DCM
  4. washwashed with a saturated aqueous solution of Na2CO3
  5. extractionThe aqueous layer was extracted with DCM
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-87bdca2f55ab4bdaa075091206a6f21e
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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