Hydrochloric Acid → HCID 86687922, compound

HRID 2401461Notes

Reaction equation

HRID 2401461 reaction equation
Br[CH2:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([N+:14]([O-:16])=[O:15])=[CH:8][C:4]=1[C:5]([O-])=[O:6].C[CH2:18][N:19](CC)CC.CN.CCO.Cl>CO.CCOC(C)=O>[CH3:13][O:12][C:10]1[CH:11]=[C:3]2[C:4](=[CH:8][C:9]=1[N+:14]([O-:16])=[O:15])[C:5](=[O:6])[N:19]([CH3:18])[CH2:2]2

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 6329MethylamineHCID 8471TriethylamineHCID 86687923HCID 86687923, compound

Product 1

HCID 86687922HCID 86687922, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To crude 2-(bromomethyl)-4-methoxy-5-nitrobenzoate (<4 mmol) in methanol (36 mL) was added Et3N (0.68 mL, 4.8 mmol) and methylamine in EtOH (0.6 mL, ˜8 M in EtOH, 4.8 mmol). The mixture was heated to 70° C. for 5 h. and then EtOAc (30 mL) and 2M HCl(aq) (30 mL) was added. The layers were separated and the aqueous layer was extracted with EtOAc (2×30 mL). The combined organic fractions were passed through a hydrophobic frit and the solvent was removed in vacuo. Purification of the residue via silica gel column chromatography (0-100% EtOAc in iso-hexane then EtOAc-10% MeOH in DCM) gave impure 5-methoxy-2-methyl-6-nitroisoindolin-1-one (487 mg) as a brown solid. The crude material was used directly in the next reaction without any further purification.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc (2×30 mL)
  3. customthe solvent was removed in vacuo
  4. customPurification of the residue via silica gel column chromatography (0-100% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-50582efa4057453f94fb9583fd578821
Source dataset
uspto-grants-2014_08
Patent number
US08796296B2

Reaction notes

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