4-Benzyloxyphenylacetaldehyde → HCID 23322068, compound

HRID 280272Notes

Reaction equation

HRID 280272 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][C:7](=[O:13])[NH:8]2.C([O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH:29]=O)=[CH:24][CH:23]=1)C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[OH:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][NH:1][CH2:2][CH2:3][C:4]2[CH:12]=[CH:11][CH:10]=[C:9]3[C:5]=2[CH2:6][C:7](=[O:13])[NH:8]3)=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 114134894-BenzyloxyphenylacetaldehydeHCID 233220374-(2-Aminoethyl)-1,3-dihydro-2H-indol-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 23322068HCID 23322068, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 0.9 g of 4-(2-aminoethyl)-2(3H)-indolone, 0.23 g of 4-benzyloxyphenylacetaldehyde, 0.25 g of 10% palladium-on-charcoal and 100 ml of ethanol is hydrogenated at 50 p.s.i. at 50° until the uptake of hydrogen is complete. After filtration, the mother liquors are evaporated to give 4-[2-(4-hydroxyphenethylamino)-ethyl]-2(3H)-indolone as the residue. This base in alcohol is treated with an excess of methanesulfonic acid to give the methanesulfonate salt.

Workup

  1. customat 50°
  2. filtrationAfter filtration
  3. customthe mother liquors are evaporated

Sources & evidence

ORD record
ord-c7c7e9eb37c648118c095d56bb37f520
Source dataset
uspto-grants-1986_05
Patent number
US04588740

Reaction notes

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