Ammonium formate → HCID 67491052, compound

HRID 1910731Notes

Reaction equation

HRID 1910731 reaction equation
C(=O)(O[CH:4]1[C:13]2[CH:12]=[C:11]3[O:14][CH:15](CC4C=CC=CC=4)[O:16][C:10]3=[CH:9][C:8]=2[N:7]([C:24](=[O:26])[CH3:25])[CH:6]([CH3:27])[CH2:5]1)N.C([O-])=O.[NH4+:32].[H][H]>C(O)C.[C].[Pd]>[NH2:32][CH:4]1[C:13]2[CH:12]=[C:11]3[O:14][CH2:15][O:16][C:10]3=[CH:9][C:8]=2[N:7]([C:24](=[O:26])[CH3:25])[CH:6]([CH3:27])[CH2:5]1

Participants

6

Reactant 3

HCID 2723923Ammonium formateHCID 66700039HCID 66700039, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67491052HCID 67491052, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

[Step 4] 375 mg (0.96 mmol) of the benzyl-5-acetyl-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]quinolin-8-yl carbamate were dissolved in 4 mL of ethanol followed by adding 242 mg (3.84 mmol) of ammonium formate and further adding 100 mg of palladium carbon. The system was replaced with hydrogen followed by stirring for 1 hour. Following completion of the reaction, the reaction liquid was filtered with celite and the filtrate was concentrated under reduced pressure. The residue was dissolved in chloroform, washed with saturated aqueous sodium bicarbonate solution and dehydrated with anhydrous sodium sulfate. The solution was concentrated under reduced pressure to obtain 225 mg (including impurities) of 1-(8-amino-6-methyl-7,8-dihydro-[1,3]dioxolo[4.5-g]quinolin-5(6H)-yl)ethanone in the form of a yellow oil.

Workup

  1. customcompletion of the reaction
  2. customthe reaction liquid
  3. filtrationwas filtered with celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in chloroform
  6. washwashed with saturated aqueous sodium bicarbonate solution
  7. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d97b5641513d485c879d4969e5ccf360
Source dataset
uspto-grants-2013_12
Patent number
US08604030B2

Reaction notes

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