Diethyl Ether → HCID 22115821, compound

HRID 1637181Notes

Reaction equation

HRID 1637181 reaction equation
[ClH:1].[N+:2]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][N:11]([CH3:15])[CH2:12]2)=[CH:7][CH:6]=1)([O-])=O.CCOCC>[Pd].C(O)C>[ClH:1].[NH2:2][C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][N:11]([CH3:15])[CH2:12]2)=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 22115827HCID 22115827, compound

Product 1

HCID 22115821HCID 22115821, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent3×

Procedure

A suspension of 3.98 g (17.5 mmol) of 7-nitro-2-methyl-1,2,3,4-tetrahydroisoquinoline hydrochloride and 0.4 g of 10% palladium on carbon in 200 ml of ethanol was hydrogenated at 50 psi for 2 h. The catalyst was filtered and washed with a small amount of water. The filtrate was concentrated yielding an aqueous solution. Absolute ethanol was added and evaporated driving off the excess water until a solid was produced. This solid was dissolved in hot ethanol (60 ml) and ether was added slowly to induce crystallization. The product was collect to give 3.38 g (97%) of the title compound as an off-white solid, m.p. 114-9° C.

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with a small amount of water
  3. concentrationThe filtrate was concentrated
  4. customyielding an aqueous solution
  5. customevaporated
  6. customwas produced
  7. customcrystallization
  8. customThe product was collect

Sources & evidence

ORD record
ord-7c30cefdc1a54dcc85e9fd7c1b6d7972
Source dataset
uspto-grants-2000_03
Patent number
US06040314

Reaction notes

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