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

HRID 893919Notes

Reaction equation

HRID 893919 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 7855Acrylonitrile2×HCID 3450289H-fluorene-9-carboxamide

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Five hundred g. of 9-carbamoylfluorene was slurried in 13 liters of tetrahydrofuran under nitrogen, and the mixture was stirred and heated to 50°. Fifty ml. of Triton B was added, followed by 131 g. of acrylonitrile. The mixture was stirred at 50° for 6 hours, and 65 g. of additional acrylonitrile and 25 ml. of Triton B were added. The mixture was stirred at 50° overnight.

Workup

  1. temperatureheated to 50°
  2. additionof Triton B was added
  3. stirringThe mixture was stirred at 50° for 6 hours
  4. additionof Triton B were added
  5. stirringThe mixture was stirred at 50° overnight

Sources & evidence

ORD record
ord-6a0a285b24694cbb943d4e041e60478e
Source dataset
uspto-grants-1981_08
Patent number
US04282170

Reaction notes

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