Water → HCID 67958504, compound

HRID 527633Notes

Reaction equation

HRID 527633 reaction equation
[CH3:1][C:2]1([CH3:22])[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][N:14]=2)[CH2:4][O:3]1.O.[Cl-].[NH4+]>O1CCCC1>[CH3:1][C:2]1([CH3:22])[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:12][C:13]2[N:14]=[CH:15][C:16]([NH2:19])=[CH:17][CH:18]=2)[CH2:4][O:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 67958128HCID 67958128, compound2×

Product 1

HCID 67958504HCID 67958504, compoundYield 34.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(3,3-dimethylisochroman-5-yl)oxy-5-nitro-pyridine (Intermediate 171, 80 mg) in tetrahydrofuran (5 ml)/water (2.5 ml) iron (70 mg, 1.3 mmol) and then ammonium chloride (70 mg, 1.3 mmol) were added and the reaction mixture was stirred overnight at room temperature. The catalyst was filtered off and the residue was diluted with an aqueous saturated solution of NaHCO3 (5 ml) and extracted with ethyl acetate (3×10 ml). The organic layer was dried over sodium sulfate, filtered and evaporated and the residue was purified by flash chromatography (Biotage system) on silica gel using a 10 g SNAP column and cyclohexane/ethyl acetate 8:2 to cyclohexane/ethyl acetate 4:6 as eluents affording the title compound (25 mg) as a white solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. additionthe residue was diluted with an aqueous saturated solution of NaHCO3 (5 ml)
  3. extractionextracted with ethyl acetate (3×10 ml)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customthe residue was purified by flash chromatography (Biotage system) on silica gel using a 10 g SNAP column and cyclohexane/ethyl acetate 8:2 to cyclohexane/ethyl acetate 4:6 as eluents

Sources & evidence

ORD record
ord-a51615b8a50d4c73a5563beeb9effff4
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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