Acetic Acid → HCID 66991936, compound

HRID 557428Notes

Reaction equation

HRID 557428 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[C:8]([N+:13]([O-:15])=[O:14])[CH:7]=[CH:6][C:5]=2[CH:16]=O.[C:18]([O:24][CH:25]([CH3:27])[CH3:26])(=[O:23])[CH2:19][C:20]([CH3:22])=O.[NH2:28]/[C:29](/[CH3:33])=[CH:30]\[C:31]#[N:32].C(O)(=O)C>CC(O)C>[C:31]([C:30]1[CH:16]([C:5]2[CH:6]=[CH:7][C:8]([N+:13]([O-:15])=[O:14])=[C:9]3[C:4]=2[O:3][C:2]([CH3:1])=[CH:11][C:10]3=[O:12])[C:19]([C:18]([O:24][CH:25]([CH3:27])[CH3:26])=[O:23])=[C:20]([CH3:22])[NH:28][C:29]=1[CH3:33])#[N:32]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 68329Isopropyl acetoacetateHCID 5325263(2Z)-3-Amino-2-butenenitrileHCID 578286522-Methyl-5-nitro-4-oxo-4H-1-benzopyran-8-carbaldehyde

Product 1

HCID 66991936HCID 66991936, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

32 mg (0.137 mmol) of 2-methyl-5-nitro-4-oxo-4H-chromene-8-carbaldehyde are dissolved with 19.7 mg (0.137 mmol) of isopropyl acetoacetate, 11.26 mg (0.137 mmol) of 3-aminocrotononitrile and 8.24 mg (0.137 mmol) of acetic acid in 3 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. 13 mg (22.3% 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-9f6244508bec478b98dd8281d4cf3df0
Source dataset
uspto-grants-2011_11
Patent number
US08058447B2

Reaction notes

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