Ammonia → HCID 21410108, compound

HRID 1283931Notes

Reaction equation

HRID 1283931 reaction equation
C([O:3][C:4]([C:6]12[CH2:17][CH2:16][CH2:15][CH:8]([C:9]3[C:14]1=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:7]2=[N:18]O)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].N.Cl.C(C12C(N)C(CC3C=CC(OC)=CC=31)CCCC2)C1C=CC=CC=1>CCOCC.C(O)C.O1CCCC1>[NH2:18][CH:7]1[CH:8]2[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:6]1([CH2:4][OH:3])[CH2:17][CH2:16][CH2:15]2

Participants

9

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 70637156HCID 70637156, compoundHCID 88820937HCID 88820937, compound

Product 1

HCID 21410108HCID 21410108, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-ethoxycarbonyl-1,3-propano-2-indanone oxime (1.9 g.) and lithium aluminum hydride (1.6 g.) and 100 ml. of tetrahydrofuran is heated at its reflux temperature under dry nitrogen for 40 hours and allowed to stand for 3 days at room temperature. A few ml. of concentrated aqueous ammonia is added and after 15 minutes stirring the mixture is filtered. The filter cake is washed twice with isopropanol containing a little ammonia. The combined filtrates are concentrated to give 1.6 g. of oil which when treated with hydrogen chloride in ether and ethanol gives 1.2 g. of crystalline hydrochloride salt of the title product with m.p. 217°- 220°.

Workup

  1. temperaturereflux temperature under dry nitrogen for 40 hours
  2. filtrationis filtered
  3. washThe filter cake is washed twice with isopropanol containing a little ammonia
  4. concentrationThe combined filtrates are concentrated
  5. customto give 1.6 g
  6. customgives 1.2 g

Sources & evidence

ORD record
ord-0d96246ee01e40dca3c046675e8c4631
Source dataset
uspto-grants-1976_08
Patent number
US03976696

Reaction notes

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