Water → HCID 67112923, compound

HRID 2284313Notes

Reaction equation

HRID 2284313 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH2:10])[CH:8]=2)[CH:3]=[CH:2]1.[OH-:11].[K+].[OH2:13]>CO.C(Cl)Cl>[N+:1]([C:9]1[CH:4]=[CH:5][C:6]([C:3]2[C:4]3[C:9](=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=3)[NH:1][CH:2]=2)=[CH:7][CH:8]=1)([O-:13])=[O:11]

Participants

6

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 2560966-Aminoindole

Product 1

HCID 67112923HCID 67112923, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of the protected indol-6-amine (300 mg, 0.76 mmol) in methanol (9.00 mL) was added potassium hydroxide (941 mg, 16.8 mmol). The reaction was warmed to 70° C. for 4 h. After that time, the reaction was diluted with water (10.0 mL) and methylene chloride (15.0 mL) and the organic phase was removed. The aqueous layer was extracted with methylene chloride (3×15.0 mL), and the combined organic phases were concentrated. The crude residue that remained was purified by flash chromatography (10-25-50% ethyl acetate/hexane) to give a burgundy red solid for 3-(4-nitrophenyl)-1H-indol-6-amine (66.3 mg, 0.26 mmol, 34%).

Workup

  1. customthe organic phase was removed
  2. extractionThe aqueous layer was extracted with methylene chloride (3×15.0 mL)
  3. concentrationthe combined organic phases were concentrated
  4. customThe crude residue that remained was purified by flash chromatography (10-25-50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4b62f787a4474c388104ba0447d9a540
Source dataset
uspto-grants-2015_09
Patent number
US09144557B2

Reaction notes

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