Formic Acid → HCID 136034483, compound

HRID 1170067Notes

Reaction equation

HRID 1170067 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([N:15]2[N:19]=[C:18]3[CH:20]=[CH:21][C:22]([O:24][CH3:25])=[CH:23][C:17]3=[N:16]2)[C:12]([OH:26])=[C:11]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:10]=1)C1C=CC=CC=1.C(O)=O.C([O-])=O.[NH4+]>C(O)C.O.[Pd]>[C:27]([C:11]1[CH:10]=[C:9]([OH:8])[CH:14]=[C:13]([N:15]2[N:19]=[C:18]3[CH:20]=[CH:21][C:22]([O:24][CH3:25])=[CH:23][C:17]3=[N:16]2)[C:12]=1[OH:26])([CH3:30])([CH3:28])[CH3:29]

Participants

7

Reactant 3

HCID 284Formic AcidHCID 2723923Ammonium formateHCID 59551959HCID 59551959, compound

Product 1

HCID 136034483HCID 136034483, compoundYield 52.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of (XIII) (3.1 Kg) in ethanol (52 L), was charged a slurry of 10% Pd/C (300 g in 750 ml water) under nitrogen atmosphere. Formic acid (1.16 L) was added followed by addition of solution of ammonium formate (1.452 Kg) in DM water (755 ml). The reaction mixture was heated at 50° C. for 6 hr. The reaction mixture was cooled to room temperature and filtered. DM Water (31 L) was added to the filtrate, stirred and extracted with toluene (62 L). The organic layer was separated and washed with of (1:1) water: ethanol mixture (31 L). The organic layer was dried on sodium sulfate and evaporated up to 80%. The residual liquid was cooled to 0-5° C., filtered and dried at 50° C. for 1 hr to give the title product (XIV) (1.254 Kg). If required, the product was leached with methanol to obtain required purity.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. additionDM Water (31 L) was added to the filtrate
  4. extractionextracted with toluene (62 L)
  5. customThe organic layer was separated
  6. washwashed with of (1:1) water
  7. customThe organic layer was dried on sodium sulfate
  8. customevaporated up to 80%
  9. temperatureThe residual liquid was cooled to 0-5° C.
  10. filtrationfiltered
  11. customdried at 50° C. for 1 hr

Sources & evidence

ORD record
ord-ab7be4b4caa14ac3bd7b07bcd6d36ed5
Source dataset
uspto-grants-2010_11
Patent number
US07825257B1

Reaction notes

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