Acetone → 2-(Hydroxymethyl)-5-methoxy-1-methyl-1H-indole-4,7-dione

HRID 968480Notes

Reaction equation

HRID 968480 reaction equation
NC1C(OC)=CC=[C:7]2[C:3]=1[CH:4]=[C:5]([CH2:14][OH:15])[N:6]2C.[C:16]([O:19][CH2:20][CH3:21])(=O)C.[OH2:22].[CH3:23][C:24]([CH3:26])=[O:25]>P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+]>[OH:15][CH2:14][C:5]1[N:6]([CH3:7])[C:23]2[C:24](=[O:25])[CH:26]=[C:20]([O:19][CH3:16])[C:21](=[O:22])[C:3]=2[CH:4]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 8857Ethyl AcetateHCID 18762535(4-Amino-5-methoxy-1-methyl-1H-indol-2-yl)methanol

Product 1

HCID 103985812-(Hydroxymethyl)-5-methoxy-1-methyl-1H-indole-4,7-dioneYield 87%

Reagents, catalysts & solvents 1

HCID 24243Trisodium PhosphateSolvent

Procedure

A solution of potassium nitrosodisulfonate (KSO3)2NO (590 mg, 2.2 mmol) in sodium phosphate buffer (0.4 M, pH=6, 13 mL) was added to a solution of 11 (130 mg, 0.63 mmol) in acetone (8 mL). The reaction mixture was stirred for 1 h at room temperature, ethyl acetate and water were added, and the aqueous layer was extracted (EtOAc, 3×). The combined organic layers were dried over Na2SO4 and evaporated. Column chromatography of the crude product (EtOAc) afforded 12 (122 mg, 87%) as an orange solid; Rf=0.62 (EtOAc); 1H NMR (CDCl3): δ 6.58 (1H, s), 5.67 (1H, s), 4.68 (2H, s), 4.03 (3H, s), 3.83 (3H, s).

Workup

  1. extractionthe aqueous layer was extracted (EtOAc, 3×)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-bd03dd63e87f4adfb907ee6d5dbd7341
Source dataset
uspto-grants-2007_12
Patent number
US07304046B2

Reaction notes

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