Formaldehyde → Indole-2,3-dione, 1-(hydroxymethyl)-

HRID 231031Notes

Reaction equation

HRID 231031 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3].C=O.[O:14]1CCOC[CH2:15]1>O>[OH:14][CH2:15][N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 7054IsatinHCID 312751,4-Dioxane

Product 1

HCID 39834Indole-2,3-dione, 1-(hydroxymethyl)-Yield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Isatin (25 g, 0.17 mol) and 30% formalin (30 ml, 0.3 mol) were added to a mixture of dioxane (10 ml) and water (20 ml) and the mixture was heated at 100° C. for 5 hours. The reaction mixture was cooled and crystals formed were filtered off. N-hydroxymethylisatin (28 g, yield 93%) was obtained. The melting point was 138° C. (decomposed).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customcrystals formed
  3. filtrationwere filtered off

Sources & evidence

ORD record
ord-e300c7d5fad146689fff82c67bdf00df
Source dataset
uspto-grants-1989_07
Patent number
US04845020

Reaction notes

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