Ammonia → HCID 20308046, compound

HRID 1763858Notes

Reaction equation

HRID 1763858 reaction equation
[C:1]1([C:14]([OH:16])=[O:15])[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.N.[Li]>C(O)C>[CH:1]1([C:14]([OH:16])=[O:15])[CH:13]2[CH:5]([C:6]3[C:11]([CH2:12]2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 80468Fluorene-1-carboxylic acidHCID 3028194Lithium

Product 1

HCID 20308046HCID 20308046, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 21.0 g (0.10 mole) of fluorene-1-carboxylic acid in 25 ml of absolute ethanol is added to 500 ml of liquid ammonia and the solution treated portionwise with 4.2 g (0.60 mole) of lithium cut in small pieces. After evaporation of the NH3, the residue is cooled in ice and treated first with water and then with sufficient conc. HCl to render it strongly acidic. The crude partially reduced product is filtered off and dissolved in acetic acid. Reduction of the solution over 1 g of PtO2 under up to 55 psi of H2 is complete after about 1 equivalent of H2 is taken up. The solution is freed of catalyst and taken to dryness. Recrystallization from hexane affords the desired product, mp 138-139°.

Workup

  1. customAfter evaporation of the NH3
  2. temperaturethe residue is cooled in ice
  3. additiontreated first with water
  4. filtrationThe crude partially reduced product is filtered off
  5. dissolutiondissolved in acetic acid
  6. customRecrystallization from hexane

Sources & evidence

ORD record
ord-887c60b5bd6c4767b719a3b902b47fba
Source dataset
uspto-grants-1978_09
Patent number
US04113726

Reaction notes

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