Ammonium formate → HCID 22640493, compound

HRID 2415123Notes

Reaction equation

HRID 2415123 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([Cl:22])[CH:20]=3)[CH2:15][CH2:14][N:13]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O.C([O-])=O.[NH4+]>CO.[Pd]>[NH2:9][C:8]1[CH:7]=[CH:6][C:5]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([Cl:22])[CH:20]=3)[CH2:15][CH2:14][N:13]=2)=[CH:4][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 22640451HCID 22640451, compound2×

Product 1

HCID 22640493HCID 22640493, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3 g of 1-(3-methoxy4-nitrophenyl)-7chloro-3,4-dihydroisoquinoline (starting compound B1) are suspended in methanol, and 2.4 g of ammonium formate and 60 mg of palladium on charcoal (10%) are added to this suspension. The reaction mixture is stirred at RT for 5 h, filtered through Celite and concentrated. The residue is purified by flash chromatography on silica gel. It is stirred out of diethyl ether/n-hexane, filtered with suction and dried. 2.4 g of the title compound are obtained.

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated
  3. customThe residue is purified by flash chromatography on silica gel
  4. stirringIt is stirred out of diethyl ether/n-hexane
  5. filtrationfiltered with suction
  6. customdried

Sources & evidence

ORD record
ord-b98c1d1010df4dd7b3696c3921b694a5
Source dataset
uspto-grants-2004_11
Patent number
US06818651B2

Reaction notes

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