Hydrochloric Acid → HCID 15733261, compound

HRID 2397574Notes

Reaction equation

HRID 2397574 reaction equation
[C:1]([CH2:3][N:4]1[C:12]2[C:7](=[CH:8][C:9]([Cl:13])=[CH:10][CH:11]=2)[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:5]1[C:20]([O:22][CH2:23][CH3:24])=[O:21])#[N:2].Cl.[H][H]>C(O)C.[Pt](=O)=O>[NH2:2][CH2:1][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][C:9]([Cl:13])=[CH:10][CH:11]=2)[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:5]1[C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 15733239HCID 15733239, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15733261HCID 15733261, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A suspension of ethyl 1-cyanomethyl-3-phenyl-5-chloroindole-2-carboxylate (12 grams, 0.035 mole), and 0.15 grams of platinum dioxide in 200 ml absolute ethanol containing 45 ml of concentrated hydrochloric acid is shaken with hydrogen at 45 psi and 45° C, in a standard Parr apparatus. Hydrogenation is stopped after 5.5 lbs. of pressure drop is observed. After removal of catalyst by filtration the filtrate is taken to dryness under reduced pressure. The solid is stirred with water and refiltered and dried. This affords 13 grams of the hydrochloride, m.p. 196°-98° C. A sample is crystallized from ethanol, washed with acetone and dried. This material melts at 205°-206° C.

Workup

  1. customAfter removal of catalyst
  2. filtrationby filtration the filtrate
  3. customdried
  4. customA sample is crystallized from ethanol
  5. washwashed with acetone
  6. customdried

Sources & evidence

ORD record
ord-c13de76d2da540f1803eee8bf8769fcc
Source dataset
uspto-grants-1977_05
Patent number
US04022778

Reaction notes

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