Formaldehyde → 5,6-Dihydroxy-N-methylisoindoline hydrobromide

HRID 704459Notes

Reaction equation

HRID 704459 reaction equation
[BrH:1].[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[OH:12])[CH2:8][NH:7][CH2:6]2.[CH:13]([O-])=O.[Na+].C=O>C(O)=O>[BrH:1].[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[OH:12])[CH2:8][N:7]([CH3:13])[CH2:6]2

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 2723810Sodium FormateHCID 200743492,3-dihydro-1H-isoindole-5,6-diol hydrobromide

Product 1

HCID 140984225,6-Dihydroxy-N-methylisoindoline hydrobromideYield 72.3%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
80 °C

Procedure

15.39 g (66 mmol) of 5,6-dihydroxyisoindoline hydrobromide and 4.48 g (66 mmol) of sodium formate were dissolved in 100 ml of a 50% formic acid aqueous solution, and then 5.17 ml (70 mmol) of 37% formalin was added thereto. The mixture was heated at 80° C. for 4 hours. Then, the reaction solvent was distilled off under reduced pressure, and 200 ml of 23% hydrobromic acid was added to the residue. The mixture was subjected to active carbon treatment. The filtrate was again evaporated under reduced pressure to dryness, and the crystalline residue was recrystallized from water to obtain 11.74 g (yield: 72.3%) of the above identified compound.

Workup

  1. distillationThen, the reaction solvent was distilled off under reduced pressure, and 200 ml of 23% hydrobromic acid
  2. additionwas added to the residue
  3. customThe filtrate was again evaporated under reduced pressure to dryness
  4. customthe crystalline residue was recrystallized from water
  5. customto obtain 11.74 g (yield: 72.3%) of the

Sources & evidence

ORD record
ord-8103f4452ed944e8971517097f65c53b
Source dataset
uspto-grants-1991_01
Patent number
US04987235

Reaction notes

Loading…