Ammonia → HCID 15075950, compound

HRID 1283731Notes

Reaction equation

HRID 1283731 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2([OH:22])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH2:17][CH2:18][C:19]#[N:20])[C:9]2=[O:21])[CH:5]=[CH:6][CH:7]=1.N.[H][H].Cl.NCCCN1C2C(=CC=CC=2)C(C2C=CC=C(Cl)C=2)(O)C1=O.Cl>[Ni].C(O)C.CCOCC.C(O)(C)C>[NH2:20][CH2:19][CH2:18][CH2:17][N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)([OH:22])[C:9]1=[O:21]

Participants

10

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 21516625HCID 21516625, compoundHCID 21516632HCID 21516632, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15075950HCID 15075950, compound

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Procedure

The nitrile of Example 1 (1.57 g.) was reduced at 40 p.s.i. and 40°C in the presence of Raney Nickel W2 (2.g.) in absolute ethanol half saturated with dry ammonia (50 ml.). Uptake ceased when slightly more than 2 equivalents of hydrogen had been taken up. The catalyst was filtered off, the ethanol solution evaporated to leave a green oil which gave 1.22 g. microcrystals, m.p. 250°-252°(decomp), of 1-(3-aminopropyl)- 3-(m-chlorophenyl)- 3-hydroxyindolin-2-one hydrochloride on treatment with isopropanol and hydrogen chloride in dry ether.

Workup

  1. custom40°C
  2. filtrationThe catalyst was filtered off
  3. customthe ethanol solution evaporated
  4. customto leave a green oil which
  5. customgave 1.22 g

Sources & evidence

ORD record
ord-262cb73b397a4850b64e3329c26beb4d
Source dataset
uspto-grants-1976_08
Patent number
US03976645

Reaction notes

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