Diethyl Ether → HCID 69803611, compound

HRID 1070533Notes

Reaction equation

HRID 1070533 reaction equation
[C:1]1([C:7]2[CH2:12][C:11](=C3C(=O)C4C(=CC=CC=4)C3=O)[CH:10]=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[NH2:25][NH2:26].CC[O:29][CH2:30][CH3:31]>>[C:1]1([C:7]2[C:12]([CH2:5][C:4]3[C:3]4[C:31](=[CH:12][CH:7]=[CH:1][CH:2]=4)[C:30](=[O:29])[NH:26][N:25]=3)=[CH:11][CH:10]=[CH:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 24654Hydrazine hydrate (1:1)HCID 69800740HCID 69800740, compound

Product 1

HCID 69803611HCID 69803611, compoundYield 86%

Conditions

Temperature
130 °C

Procedure

A mixture of 2-(2-phenyl-pyridin-4-ylidene)-indan-1,3-dione (3.1 g, 10.4 mmol) and hydrazine hydrate (9.7 mL) was stirred at 130° C. under argon for 5 h. The reaction mixture was cooled and filtered. The resultant tacky solid was dissolved in ethyl acetate (250 mL) and then washed with water (2×50 mL) and brine (1×50 mL). The organic layer was dried over MgSO4, filtered, and evaporated in vacuo. Trituration from ether afforded the title compound as a beige solid (2.82 g, 9.0 mmol, 86% yield). 1H-NMR (DMSO-d6) 12.59 (broad s, 1H), 8.52 (d, J=4.6, 1H), 8.24 (dd, J=7.7, 1.0,1H), 7.95 to 8.03 (m, 4H), 7.78 to 7.91 (m, 2H), 7.40 to 7.49 (m, 3H), 7.21 (d, J=6.5, 1H), 4.39 (s, 2H); MS ES 314 (M+H)+, calc.313; TLC (1:2:8 v/v methanol-acetone-dichloromethane) Rf=0.40.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. dissolutionThe resultant tacky solid was dissolved in ethyl acetate (250 mL)
  4. washwashed with water (2×50 mL) and brine (1×50 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-1d22ee64a082409888d44c1dccf9bae0
Source dataset
uspto-grants-2005_06
Patent number
US06903101B1

Reaction notes

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