Hydrochloric Acid → HCID 23374586, compound

HRID 865702Notes

Reaction equation

HRID 865702 reaction equation
[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:8]2[CH2:11][C:10](=[CH:12][C:13]([O:15][CH3:16])=[O:14])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>[OH-].[OH-].[Pd+2].CO>[C:17]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:11][CH:10]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH2:9]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 10891697HCID 10891697, compound

Product 1

HCID 23374586HCID 23374586, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of the compound from step 3 (21.0 g, 71.7 mmol), Pd(OH)2 (3.0 g, 20% on C), methanol (500 ml) and 2 N HCl (37 ml) was hydrogenated on a Parr shake apparatus for 2 h. The catalyst was removed by filtration through celite and the solvents removed under vacuum. Saturated K2CO3 solution was added (50 ml) and extracted with CH2Cl2 (2×250 ml). The combined extracts were washed with H2O (250 ml) and brine (100 ml), dried (Na2SO4) and evaporated to give the title-product as a pale yellow oil (19.3 g). δ (360 MHz, CDCl3) 2.58 (2H, d, J=7.3 Hz, CH2), 2.75-2.81 (3H, m, 2 of CH of CH2 and CH), 3.35-3.38 (2H, m, 2 of CH of CH2), 3.62 (3H, s, CO2Me), 4.31 (1H, s, CH), 7.14-7.18, 7.23-7.27 and 7.38-7.40 (total 10H, each m, Ar--H).

Workup

  1. customThe catalyst was removed by filtration through celite
  2. customthe solvents removed under vacuum
  3. additionSaturated K2CO3 solution was added (50 ml)
  4. extractionextracted with CH2Cl2 (2×250 ml)
  5. washThe combined extracts were washed with H2O (250 ml) and brine (100 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-cc3a8a569c9c4757b09c1dd7b39aed2e
Source dataset
uspto-grants-1996_10
Patent number
US05567726

Reaction notes

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