Formaldehyde → Methyl 2-methyl-2,3-dihydro-1H-isoindole-5-carboxylate

HRID 1875334Notes

Reaction equation

HRID 1875334 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH2:3][NH:2]1.[CH2:14]=O>C(O)=O>[CH3:14][N:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[C:6]([C:10]([O:12][CH3:13])=[O:11])[CH:5]=2)[CH2:1]1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 19828496Methyl isoindoline-5-carboxylate

Product 1

HCID 57423971Methyl 2-methyl-2,3-dihydro-1H-isoindole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
70 °C

Procedure

1.2 g (6.6 mmol) methyl 2,3-dihydro-1H-isoindole-5-carboxylate are dissolved in 5 ml formic acid, combined with 2 ml formalin solution (37% solution in water), heated to 70° C. for 3.5 hours and stirred for 16 hours at RT. The reaction mixture is evaporated down i. vac. and combined with 0.1 N sodium hydroxide solution and extracted three times with ethyl acetate. The combined organic phases are dried on sodium sulphate, filtered and evaporated down i. vac.

Workup

  1. customThe reaction mixture is evaporated down i
  2. extractionextracted three times with ethyl acetate
  3. customThe combined organic phases are dried on sodium sulphate
  4. filtrationfiltered
  5. customevaporated down i

Sources & evidence

ORD record
ord-346ce398e0a049cdb077ad78837f807f
Source dataset
uspto-grants-2012_11
Patent number
US08309542B2

Reaction notes

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