Acrylonitrile → 9-(2-Cyanoethyl)-9H-fluorene-9-carboxamide

HRID 893918Notes

Reaction equation

HRID 893918 reaction equation
[C:1]([CH:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)(=[O:3])[NH2:2].[C:17](#[N:20])[CH:18]=[CH2:19]>O1CCCC1>[C:1]([C:4]1([CH2:19][CH2:18][C:17]#[N:20])[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)(=[O:3])[NH2:2]

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 3450289H-fluorene-9-carboxamide

Product 1

HCID 30188199-(2-Cyanoethyl)-9H-fluorene-9-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

One hundred g. of 9-carbamoylfluorene was slurried in 3375 ml. of tetrahydrofuran in a 5-liter flask. The mixture was heated to 45° with stirring, and to it was added 10 ml. of Triton B. The mixture was stirred for 15 minutes at constant temperature, and 26.2 g. of acrylonitrile was then added in one portion. The mixture was stirred at the reflux temperature for 3 hours, and was then allowed to cool to room temperature. The mixture was then concentrated under vacuum to a solid, which was purified as described in Example 1 above to obtain 110 g. of product, analytically identical to the product of Example 1.

Workup

  1. temperatureThe mixture was heated to 45°
  2. additionto it was added 10 ml
  3. stirringThe mixture was stirred for 15 minutes at constant temperature, and 26.2 g
  4. stirringThe mixture was stirred at the reflux temperature for 3 hours
  5. concentrationThe mixture was then concentrated under vacuum to a solid, which
  6. customwas purified
  7. customto obtain 110 g

Sources & evidence

ORD record
ord-a78c83178ab34b7db593c36258dfff98
Source dataset
uspto-grants-1981_08
Patent number
US04282170

Reaction notes

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