Acetic Acid → HCID 15979087, compound

HRID 557397Notes

Reaction equation

HRID 557397 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[CH:13]=O.O=[C:16]([CH3:22])[CH2:17][C:18]([O:20][CH3:21])=[O:19].[NH2:23]/[C:24](/[CH3:28])=[CH:25]\[C:26]#[N:27].C(O)(=O)C>CC(O)C>[C:26]([C:25]1[CH:13]([C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[O:3][C:2]([CH3:1])=[CH:11][C:10]3=[O:12])[C:17]([C:18]([O:20][CH3:21])=[O:19])=[C:16]([CH3:22])[NH:23][C:24]=1[CH3:28])#[N:27]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7757Methyl acetoacetateHCID 5325263(2Z)-3-Amino-2-butenenitrileHCID 133748832-Methyl-4-oxo-4H-chromene-8-carbaldehyde

Product 1

HCID 15979087HCID 15979087, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

100 mg (0.53 mmol) of 2-methyl-4-oxo-4H-chromene-8-carbaldehyde are dissolved with 61.7 mg (0.53 mmol) of methyl 3-oxobutanoate, 43.6 mg (0.53 mmol) of 3-aminocrotononitrile and 31.9 mg (0.53 mmol) of acetic acid in 5 ml of 2-propanol and heated under reflux under argon for 4 h. After cooling to room temperature, the crystallized product is filtered off and washed with 2-propanol and, diethyl ether. 97 mg (52% of theory) of the title compound are obtained as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux under argon for 4 h
  3. filtrationthe crystallized product is filtered off
  4. washwashed with 2-propanol and, diethyl ether

Sources & evidence

ORD record
ord-3e2c27a8a4e247df88f8039942a364d7
Source dataset
uspto-grants-2011_11
Patent number
US08058447B2

Reaction notes

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