Benzoic Acid → 2-cyano-2-(5,6-dimethoxy-3,3-dimethyl-indan-1-ylidene)-N-prop-2-ynyl-acetamide

HRID 2228349Notes

Reaction equation

HRID 2228349 reaction equation
C([O:3][C:4](=O)[C:5]([C:21]#[N:22])=[C:6]1[C:14]2[C:9](=[CH:10][C:11]([O:17][CH3:18])=[C:12]([O:15][CH3:16])[CH:13]=2)[C:8]([CH3:20])([CH3:19])[CH2:7]1)C.[C:24]([CH2:26][C:27](NCC#C)=O)#[N:25].N1CCCC1.C(O)(=O)C1C=CC=CC=1>C1(C)C=CC=CC=1.O>[C:21]([C:5](=[C:6]1[C:14]2[C:9](=[CH:10][C:11]([O:17][CH3:18])=[C:12]([O:15][CH3:16])[CH:13]=2)[C:8]([CH3:20])([CH3:19])[CH2:7]1)[C:4]([NH:25][CH2:24][C:26]#[CH:27])=[O:3])#[N:22]

Participants

7

Reactant 4

HCID 243Benzoic AcidHCID 31268PyrrolidineHCID 184695792-cyano-N-(prop-2-yn-1-yl)acetamideHCID 54568492Cyano-(2,3-dihydro-5,6-dimethoxy-3,3-dimethyl-1H-inden-1-ylidene)acetic Acid Ethyl Ester

Product 1

HCID 537630542-cyano-2-(5,6-dimethoxy-3,3-dimethyl-indan-1-ylidene)-N-prop-2-ynyl-acetamideYield 49.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

A 50 ml reaction flask equipped with a water separator and a reflux condenser was charged with 2.2 g of 2,3-dihydro-5,6-dimethoxy-3,3-dimethyl-1H-inden-1-one (see Example 1), 1.2 g of 2-cyano-N-prop-2-ynyl-acetamide (see above), catalytic amounts of pyrrolidine, and benzoic acid in 20 ml of toluene. The reaction mixture was refluxed for 24 hours with simultaneous separation of water. Then, the product in the cold reaction mixture was filtered off and recrystallized in ethylacetate to yield 1.13 g of white crystals, m.p. 202° C.-205° C. UV 362 nm (ε=24′992). Solubility: 0.04% in CÉTIOL LC

Workup

  1. customA 50 ml reaction flask
  2. customThen, the product in the cold reaction mixture
  3. filtrationwas filtered off
  4. customrecrystallized in ethylacetate

Sources & evidence

ORD record
ord-977eda4c26f94a08a72c5bb4fee4b043
Source dataset
uspto-grants-2002_07
Patent number
US06416746B1

Reaction notes

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