Sodium Dithionite → HCID 43518240, compound

HRID 244357Notes

Reaction equation

HRID 244357 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([CH3:20])[CH:19]=1)[O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][C:7]=1[N+:14]([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+]>C1COCC1.O>[NH2:14][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:6]=1[O:5][C:4]1[CH:3]=[C:2]([CH3:1])[CH:19]=[C:18]([CH3:20])[CH:17]=1)[C:10]#[N:11]

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 34039741HCID 34039741, compound

Product 1

HCID 43518240HCID 43518240, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

A solution of compound 21 (15.00 g, 55.91 mmol) in THF (250 mL) was added a solution of sodium hydrosulfite (58.41 g, 335.5 mmol) in water (75 mL). The reaction mixture was stirred at 90° C. After 24 hrs, the starting material was consumed as monitored with TLC (10% EtOAc in hexanes) and reaction mixture was removed from heat. The reaction mixture was concentrated in vacuo until product precipitated in remaining water. The precipitate was collected via vacuum filtration and washed with water. The product was dried overnight in vacuum at 40° C. to afford compound 22. (12.681 g, 95.2% yield, 99.9% HPLC purity). 1H NMR (500 MHz, DMSO-d6): δ 7.08 (d, J=2 Hz, 1H), 6.91 (dd, J1=8 Hz, J2=2 Hz, 1H), 6.80 (s, 1H), 6.73 (d, J=8 Hz, 1H), 6.63 (s, 2H), 5.47 (s, 2H), 2.24 (s, 6H).

Workup

  1. customthe starting material was consumed
  2. customas monitored with TLC (10% EtOAc in hexanes) and reaction mixture
  3. customwas removed
  4. temperaturefrom heat
  5. concentrationThe reaction mixture was concentrated in vacuo until product
  6. customprecipitated
  7. filtrationThe precipitate was collected via vacuum filtration
  8. washwashed with water
  9. customThe product was dried overnight in vacuum at 40° C.

Sources & evidence

ORD record
ord-177c8162209344b5b560413d383d70fb
Source dataset
uspto-grants-2014_02
Patent number
US08658642B2

Reaction notes

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