Ethanol → HCID 86600130, compound

HRID 1453990Notes

Reaction equation

HRID 1453990 reaction equation
[OH:1][C:2]1[C:10]2[O:9][C:8](=O)[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Br:12][C:13]1[C:14]([O:23][CH3:24])=[C:15]([O:21][CH3:22])[CH:16]=[C:17]([CH:20]=1)C=O.[C:25](#N)[CH2:26][C:27]#[N:28].[NH:30]1[CH2:35]CCCC1.C([OH:38])C>>[NH2:7][CH:8]1[N:28]([C:35]#[N:30])[CH:27]2[CH:26]([C:17]3[CH:16]=[C:15]([O:21][CH3:22])[C:14]([O:23][CH3:24])=[C:13]([Br:12])[CH:20]=3)[CH:25]=[C:5]3[C:6]([O:38][C:2](=[O:1])[CH:3]=[CH:4]3)=[C:10]2[O:9]1

Participants

6

Reactant 5

HCID 702EthanolHCID 8010MalononitrileHCID 8082PiperidineHCID 813793-Bromo-4,5-dimethoxybenzaldehydeHCID 15588672HCID 15588672, compound

Product 1

HCID 86600130HCID 86600130, compoundYield 38%

Procedure

7-Hydroxy-3H-benzooxazol-2-one (300 mg, 1.98 mmol), 5-bromoveratraldehyde (486 mg, 1.98 mmol) and malononitrile (131 mg, 1.98 mmol) were dissolved in ethanol (12 mL). Piperidine (390 μL, 3.96 mmol) was added and the reaction was stirred at room temperature overnight. The precipitate was filtered and dried to yield 339 mg (38%) of the desired 2-amino-4-(3-bromo-4,5-dimethoxyphenyl)-3-cyano-8-oxo-4H-oxazolo[4,5-h]chromene as a light yellow powder. 1H NMR (DMSO-d6): 11.79 (s, 1H), 7.21 (brs, 2H), 6.98 (s, 1H), 6.91 (s, 1H), 6.85-6.79 (m, 2H), 4.79 (s, 1H), 3.78 (s, 3H), 3.68 (s, 3H).

Workup

  1. filtrationThe precipitate was filtered
  2. customdried

Sources & evidence

ORD record
ord-2850be4030be4b04a4ef983b3a580e45
Source dataset
uspto-grants-2009_01
Patent number
US07476741B2

Reaction notes

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