Hydrochloric Acid → HCID 67285202, compound

HRID 541068Notes

Reaction equation

HRID 541068 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][CH2:14][C:15](OCC)=[O:16])[C:8]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:7]2)([O-:3])=[O:2].C1COCC1.O.Cl>CCO>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][CH2:14][CH2:15][OH:16])[C:8]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:7]2)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 67284846HCID 67284846, compound

Product 1

HCID 67285202HCID 67285202, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution containing ethyl 3-(5-nitro-2-phenyl-1H-indol-1-yl)propanoate (prepared as described in example 1 g) (2.1 g; 6.2 mmol) in THF (20 ml) sodium borohydride (0.98 g, 24.8 mmol) and EtOH absolute (25 ml) were added; the reaction mixture was left under stirring at room temperature for 18 hours. Then water (5 ml) and HCl 2N were added to pH 6. The solution was transferred into a separating funnel, and extracted with ethyl acetate (2×50 ml). The organic phases were combined, and dried over Na2SO4. The solvent was removed by evaporation under reduced pressure and the residue was purified by flash chromatography on silica gel (n-hexane/EtOAc, n-hexane 100→70%) to give 3-(5-nitro-2-phenyl-1H-indol-1-yl)propan-1-ol (1.5 g), which was used without any further purification.

Workup

  1. additionwere added
  2. waitthe reaction mixture was left
  3. customThe solution was transferred into a separating funnel
  4. extractionextracted with ethyl acetate (2×50 ml)
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed by evaporation under reduced pressure
  7. customthe residue was purified by flash chromatography on silica gel (n-hexane/EtOAc, n-hexane 100→70%)

Sources & evidence

ORD record
ord-aa8f1eedf3bf4b9e855818a781e7c112
Source dataset
uspto-grants-2014_10
Patent number
US08871948B2

Reaction notes

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