HCID 23453171, compound → HCID 23453175, compound

HRID 1277643Notes

Reaction equation

HRID 1277643 reaction equation
[Cl:1]([O-])(=O)(=O)=O.[C:6]([CH2:8][CH2:9][CH:10]1[C:19]2[C:18]3[NH:20][C:21]4[C:26]([C:17]=3[CH2:16][CH2:15][N+:14]=2[CH2:13][CH2:12][CH2:11]1)=[CH:25][CH:24]=[CH:23][CH:22]=4)#[N:7]>CO.[Pd]>[ClH:1].[C:6]([CH2:8][CH2:9][CH:10]1[CH:19]2[N:14]([CH2:15][CH2:16][C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[NH:20][C:18]=32)[CH2:13][CH2:12][CH2:11]1)#[N:7]

Participants

4

Reactant 1

HCID 23453171HCID 23453171, compound

Product 1

HCID 23453175HCID 23453175, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2.50 g (6.6) mmoles) of the product of Example 8 are hydrogenated in 120 ml of methanol in the presence of 2.0 g of palladium-on-charcoal. After the uptake of the calculated amount of hydrogen (about 25 minutes) the catalyst is filtered off and the filtrate is evaporated in vacuo. The residue is admixed with 30 ml of water, the mixture is rendered alkaline with aqueous sodium carbonate solution, and extracted with dichloromethane. The dichloromethane solutions are combined, dried, filtered, and the filtrate is evaporated. The oily residue is dissolved in 10 ml of methanol, and the solution is acidified to pH 6 with methanolic hydrochloric acid. The separated substance is filtered off, washed with ether and dried.

Workup

  1. filtrationAfter the uptake of the calculated amount of hydrogen (about 25 minutes) the catalyst is filtered off
  2. customthe filtrate is evaporated in vacuo
  3. extractionextracted with dichloromethane
  4. customdried
  5. filtrationfiltered
  6. customthe filtrate is evaporated
  7. dissolutionThe oily residue is dissolved in 10 ml of methanol
  8. filtrationThe separated substance is filtered off
  9. washwashed with ether
  10. customdried

Sources & evidence

ORD record
ord-63db999aae6e480eb44c22a33b2847bc
Source dataset
uspto-grants-1981_07
Patent number
US04278682

Reaction notes

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