4-Bromoaniline → HCID 178509171, compound

HRID 2304428Notes

Reaction equation

HRID 2304428 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][N:9]=[C:10]([C:13]#[N:14])[C:11]#[N:12])=[CH:4][CH:3]=1.BrC1C=CC(N)=CC=1.C(#N)CC#N.O.[NH2:29][NH2:30]>>[NH2:14][C:13]1[C:10](=[N:9][NH:8][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)[C:11]([NH2:12])=[N:30][N:29]=1

Participants

5

Reactant 4

HCID 78074-BromoanilineHCID 8010MalononitrileHCID 24654Hydrazine hydrate (1:1)2×HCID 23273954(4-Bromophenyl)carbonohydrazonoyl dicyanide

Product 1

HCID 178509171HCID 178509171, compoundYield 78%

Procedure

This compound was prepared using 125 mg (0.5 mmol) of 2-[(4-bromophenyl)-hydrazono]malononitrile, which was derived from 4-bromoaniline (172 mg, 1.0 mmol) and malononitrile (1.5 mmol) as described in Example 8, and hydrazine hydrate. The hydrazine hydrate was added to the solution at a temperature of 75° C. despite the fact that the starting material had not fully dissolved. The solution cleared briefly and then a precipitate formed. The resulting solid was isolated by filtration, washed with ethanol, and dried to yield 109 mg (78%) of the title compound as a yellow solid. 1H NMR (ppm, DMSO-d6): 6.15 (br s, 4H), 7.52 (d, 2H), 7.61 (d, 2H), 10.71 (s, 1H).

Workup

  1. customThis compound was prepared
  2. dissolutionhad not fully dissolved
  3. customa precipitate formed
  4. customThe resulting solid was isolated by filtration
  5. washwashed with ethanol
  6. customdried

Sources & evidence

ORD record
ord-b132d22b2118440cba89f31e52df0f5f
Source dataset
uspto-grants-2002_08
Patent number
US06436915B1

Reaction notes

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