Malononitrile → 2,7,8-triamino-4-(3-bromo-4,5-dimethoxyphenyl)-4H-chromene-3-carbonitrile

HRID 1826976Notes

Reaction equation

HRID 1826976 reaction equation
[Br:1][C:2]1[C:3]([O:12][CH3:13])=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([CH:9]=1)[CH:7]=O.[C:14](#[N:18])[CH2:15][C:16]#[N:17].N1CCCCC1.[NH2:25][C:26]1[C:31]([NH2:32])=[CH:30][CH:29]=[CH:28][C:27]=1[OH:33]>C(O)C.O>[C:16]([C:15]1[CH:7]([C:6]2[CH:5]=[C:4]([O:10][CH3:11])[C:3]([O:12][CH3:13])=[C:2]([Br:1])[CH:9]=2)[C:28]2[C:27](=[C:26]([NH2:25])[C:31]([NH2:32])=[CH:30][CH:29]=2)[O:33][C:14]=1[NH2:18])#[N:17]

Participants

7

Reactant 4

HCID 8010MalononitrileHCID 8082PiperidineHCID 813793-Bromo-4,5-dimethoxybenzaldehydeHCID 5799372,3-Diaminophenol

Product 1

HCID 102020482,7,8-triamino-4-(3-bromo-4,5-dimethoxyphenyl)-4H-chromene-3-carbonitrileYield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 5-bromoveratraldehyde (980 mg, 4.0 mmol) and malononitrile (246 mg, 4.0 mmol) in ethanol (10 mL) was added piperidine (0.4 mL) and 2,3-diaminophenol (496 mg, 4.0 mmol). The mixture was stirred at room temperature under argon for 2 h then diluted with water (20 mL). The precipitate was filtered to yield brown solid, yielding 1.367 g (85%) of the title compound. 1H NMR (CD3OD): 6.25 (s, 1H), 6.18 25 (s, 1H), 6.34 (d, J=7.8, 1H), 6.10 (d, J=7.8, 1H), 4.43 (s, 1H), 3.68 (s, 3H), 3.64 (s, 3H).

Workup

  1. filtrationThe precipitate was filtered
  2. customto yield brown solid

Sources & evidence

ORD record
ord-96b6690b64894ddb946d7e08097f2ac8
Source dataset
uspto-grants-2006_05
Patent number
US07053117B2

Reaction notes

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