Sodium Dithionite → HCID 89650673, compound

HRID 2174213Notes

Reaction equation

HRID 2174213 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[N+:9]([C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH:22]=[CH:21][CH:20]=[C:19]2[C:23]([O:25][CH3:26])=[O:24])=[CH:14][CH:13]=1)([O-])=O>O.CCO>[NH2:9][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH:22]=[CH:21][CH:20]=[C:19]2[C:23]([O:25][CH3:26])=[O:24])=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 24489Sodium Dithionite2×HCID 14270008HCID 14270008, compound

Product 1

HCID 89650673HCID 89650673, compoundYield 54.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Sodium hydrosulphite (2.08 g, 10.15 mmoll) in water (7.5 mL) was added to a refluxing solution of (i) (1 g, 4.06 mmol) in EtOH (15 mL). After 5 minutes another solution of sodium hydrosulphite (2.08 g, 10.15 mmoll) in water (7.5 mL) was added. The mixture refluxed for 5 min After that time the mixture was poured onto water. The reaction mixture was extracted with EtOAc and DCM/iPrOH. The organic fractions were dried (MgSO4), filtered and concentrated in vacuo to give a residue that was purified by flash chromatography on silica gel, eluting with a MeOH gradient in DCM to afford the desired product (ii) (480 mg). 1H NMR (400 MHz, DMSO) δ 7.06 (dd, J=2.5, 1.9 Hz, 1H), 6.96-6.90 (m, 3H), 6.59-6.53 (m, 2H), 6.22 (dd, J=3.9, 2.6 Hz, 1H), 5.25 (s, 2H), 3.60 (s, 3H).

Workup

  1. temperatureThe mixture refluxed for 5 min After that time the mixture
  2. additionwas poured onto water
  3. extractionThe reaction mixture was extracted with EtOAc and DCM/iPrOH
  4. dry with materialThe organic fractions were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a residue that
  8. customwas purified by flash chromatography on silica gel
  9. washeluting with a MeOH gradient in DCM

Sources & evidence

ORD record
ord-3ec77086f7314d40a2bbf4ff520dc043
Source dataset
uspto-grants-2015_06
Patent number
US09060515B2

Reaction notes

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