Methanol → HCID 89815411, compound

HRID 1481192Notes

Reaction equation

HRID 1481192 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])=[CH:8][CH:9]=2)[C:4](=[O:19])[N:3]1[CH2:20][C:21]([OH:23])=[O:22].OS(O)(=O)=O.[CH3:29]O>>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])=[CH:8][CH:9]=2)[C:4](=[O:19])[N:3]1[CH2:20][C:21]([O:23][CH3:29])=[O:22]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 89815163HCID 89815163, compound

Product 1

HCID 89815411HCID 89815411, compound

Procedure

A mixture of 2-(1,3-dioxo-5-(o-tolyloxy)isoindolin-2-yl)acetic acid (10.1 g, 32.5 mmol) and concentrated H2SO4 (2.0 mL) in MeOH (41 mL) was heated to reflux with stirring for 18 hours. After cooling to room temperature, the solvent was removed in vacuo. To the residue was added sat'd NaHCO3 solution (100 mL) and EtOAc (100 mL). The layers were separated and the organic layer was dried over Mg SO4 and then concentrated in vacuo to give the title compound as white solid in 10.0 g. 1H NMR (CDCl3, 200 MHz): δ=7.78 (d, 1H, J=9.0 Hz), 7.31-7.13 (m, 5H), 6.98 (d, 1H, J=7.4 Hz), 4.40 (s, 2H), 3.75 (s, 3H), 2.18 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. customthe solvent was removed in vacuo
  4. additionTo the residue was added sat'd NaHCO3 solution (100 mL) and EtOAc (100 mL)
  5. customThe layers were separated
  6. dry with materialthe organic layer was dried over Mg SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-286850d513bd4874b5b9311f5452e4d9
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

Loading…