Acetic Acid → HCID 66991480, compound

HRID 557432Notes

Reaction equation

HRID 557432 reaction equation
[CH:1]([C:3]1[C:12]2[O:11][C:10]([CH3:13])=[CH:9][C:8](=[O:14])[C:7]=2[C:6]([C:15]#[N:16])=[CH:5][CH:4]=1)=O.[C:17]([O:23][CH:24]([CH3:26])[CH3:25])(=[O:22])[CH2:18][C:19]([CH3:21])=O.[NH2:27]/[C:28](/[CH3:32])=[CH:29]\[C:30]#[N:31].C(O)(=O)C>CC(O)C>[C:30]([C:29]1[CH:1]([C:3]2[CH:4]=[CH:5][C:6]([C:15]#[N:16])=[C:7]3[C:12]=2[O:11][C:10]([CH3:13])=[CH:9][C:8]3=[O:14])[C:18]([C:17]([O:23][CH:24]([CH3:26])[CH3:25])=[O:22])=[C:19]([CH3:21])[NH:27][C:28]=1[CH3:32])#[N:31]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 68329Isopropyl acetoacetateHCID 5325263(2Z)-3-Amino-2-butenenitrileHCID 578286138-Formyl-2-methyl-4-oxo-4H-1-benzopyran-5-carbonitrile

Product 1

HCID 66991480HCID 66991480, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

21 mg (0.09 mmol) of 8-formyl-2-methyl-4-oxo-4H-chromene-5-carbonitrile are dissolved with 14 mg (0.09 mmol) of isopropyl acetoacetate, 8 mg (0.09 mmol) of 3-aminocrotononitrile and 6 mg (0.09 mmol) of acetic acid in 2 ml of 2-propanol and heated under reflux under argon for 6 h. The solvent is removed in vacuo, and the residue is purified by preparative HPLC. 8.8 mg (22% of theory) of the title compound are obtained as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux under argon for 6 h
  3. customThe solvent is removed in vacuo
  4. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-8764b67b1af140a2b5b3c71e1ddfdce5
Source dataset
uspto-grants-2011_11
Patent number
US08058447B2

Reaction notes

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