Ammonium formate → HCID 71245449, compound

HRID 532130Notes

Reaction equation

HRID 532130 reaction equation
[CH:1](=[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=2)[O:11][CH2:10][CH:9]1[NH:20][C:21](=[O:25])[O:22][CH2:23][CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])=O.[NH4+]>CCO.O.[Pd]>[CH2:1]([CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=2)[O:11][CH2:10][CH:9]1[NH:20][C:21](=[O:25])[O:22][CH2:23][CH3:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 71245607HCID 71245607, compound

Product 1

HCID 71245449HCID 71245449, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

3.1 g (9.1 mmol) of ethyl 4-benzylidene-6-methoxychroman-3-ylcarbamate were dissolved in 80 ml of EtOH and 910 mg (0.9 mmol) Pd/C were added. Then, 5.8 g (91 mmol) of ammonium formate dissolved in 20 ml of water were added and the mixture was warmed to 70° C. and stirred for 1.5 h. The mixture was cooled to room temperature. The catalyst was filtered off and washed with EtOH/water. The filtrate was concentrated in vacuo to remove EtOH. The aqueous concentrate was extracted with ethyl acetate (2×). The combined organic phases were dried over MgSO4 and the solvent was evaporated to yield 3.2 g (9.3 mmol, quant.) of the crude product.

Workup

  1. additionwere added
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationThe catalyst was filtered off
  4. washwashed with EtOH/water
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto remove EtOH
  7. concentrationThe aqueous concentrate
  8. extractionwas extracted with ethyl acetate (2×)
  9. dry with materialThe combined organic phases were dried over MgSO4
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-bcbb7807b39c4d60b24f4b911fa95d06
Source dataset
uspto-grants-2014_10
Patent number
US08853196B2

Reaction notes

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