3-Fluoroaniline → HCID 178509198, compound

HRID 2304446Notes

Reaction equation

HRID 2304446 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][N:9]=[C:10]([C:13]#[N:14])[C:11]#[N:12])[CH:5]=[CH:6][CH:7]=1.FC1C=C(C=CC=1)N.C(CC(OC1CCCCC1)=O)#N.[OH2:35].[NH2:36]N>C(O)C>[NH2:14][C:13]1[C:10](=[N:9][NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[C:11](=[O:35])[NH:12][N:36]=1

Participants

6

Reactant 4

HCID 97423-FluoroanilineHCID 24654Hydrazine hydrate (1:1)HCID 96357Cyclohexyl cyanoacetateHCID 4199695HCID 4199695, compound

Product 1

HCID 178509198HCID 178509198, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

This compound was prepared using 2-[(3-fluorophenyl)hydrazono]malononitrile (145 mg, 0.5 mmole), which was derived from 3-fluoroaniline (111 mg, 1 mmole)) and cyclohexyl cyanoacetate (217 mg, 1.3 mmole) as described in Example 8, and hydrazine hydrate (25 mg, 0.5 mmole) in ethanol. Solids had not formed after heating the reaction at 80° C. for 40 minutes, however, analysis of the reaction solution by TLC indicated that no starting material remained. The solution was allowed to cool to room temperature and concentrated. The product was obtained after filtration as a yellow solid (73 mg). 1H NMR (ppm, DMSO-d6): 5.95 (br., s, 2H), 6.90 (m, 1H), 7.20-7.65 (m, 3H), 10.56 (br., s, 1H) 12.77 (br., s, 1H).

Workup

  1. customThis compound was prepared
  2. customSolids had not formed
  3. temperatureafter heating
  4. customthe reaction at 80° C. for 40 minutes
  5. concentrationconcentrated
  6. customThe product was obtained
  7. filtrationafter filtration as a yellow solid (73 mg)

Sources & evidence

ORD record
ord-c2ceccb492f845e68b224ee6ec0a4124
Source dataset
uspto-grants-2002_08
Patent number
US06436915B1

Reaction notes

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