HCID 12797486, compound → HCID 20448365, compound

HRID 358516Notes

Reaction equation

HRID 358516 reaction equation
[OH:1][CH:2]([CH2:16][N:17]([CH:25]([CH3:27])[CH3:26])CC1C=CC=CC=1)[CH2:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[C:7]([CH:14]=[O:15])=[CH:8][NH:9]2.[C:28]([OH:36])(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.OC1C(OCCCNC(C)C)(C=O)C2C(=CC=CC=2)N=1>[Pd].CO>[C:28]([OH:36])(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[OH:1][CH:2]([CH2:16][NH:17][CH:25]([CH3:27])[CH3:26])[CH2:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[C:7]([CH:14]=[O:15])=[CH:8][NH:9]2

Participants

5

Reactant 2

HCID 12797486HCID 12797486, compoundHCID 178457323HCID 178457323, compound

Product 1

HCID 20448365HCID 20448365, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

6.6 g. 4-[2-hydroxy-3-(N-benzylisopropylamino)-propoxy]-3-formylindole (see Example 1) are dissolved in 150 ml. methanol, mixed with 0.5 g. 10% palladiumcharcoal and hydrogenated at ambient temperature and under a hydrogen pressure of 1 bar. The reaction mixture is subsequently filtered and concentrated to a volume of about 20 ml. and the equivalent amount of benzoic acid is added thereto. After suction filtration, there are obtained 3.1 g. (44% of theory) 4-[2-hydroxy-3-(isopropylamino-propoxy]-3-formylindole benzoate; m.p. 204°-105° C.

Workup

  1. customhydrogenated at ambient temperature
  2. filtrationThe reaction mixture is subsequently filtered
  3. concentrationconcentrated to a volume of about 20 ml
  4. additionand the equivalent amount of benzoic acid is added
  5. filtrationAfter suction filtration, there
  6. customare obtained 3.1 g

Sources & evidence

ORD record
ord-a479994e5377486fa76e4373e22de888
Source dataset
uspto-grants-1984_08
Patent number
US04468520

Reaction notes

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