Hydrochloric Acid → HCID 86687918, compound

HRID 2401455Notes

Reaction equation

HRID 2401455 reaction equation
Br[CH2:2][C:3]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([O:16][CH3:17])=[CH:9][C:4]=1[C:5](OC)=[O:6].C[CH2:19][N:20](CC)CC.CN.CCO.Cl>CO.CCOC(C)=O>[CH3:17][O:16][C:10]1[CH:9]=[C:4]2[C:3]([CH2:2][N:20]([CH3:19])[C:5]2=[O:6])=[CH:12][C:11]=1[N+:13]([O-:15])=[O:14]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 6329MethylamineHCID 8471TriethylamineHCID 71513519HCID 71513519, compound

Product 1

HCID 86687918HCID 86687918, compoundYield 75.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To methyl 2-(bromomethyl)-5-methoxy-4-nitrobenzoate (212 mg, 0.7 mmol) in methanol (6 mL) was added Et3N (0.12 mL, 0.84 mmol) and methylamine in EtOH (0.11 mL, ˜8 M in EtOH, 0.84 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 6-methoxy-2-methyl-5-nitroisoindolin-1-one (117 mg, 75%) as an off-white solid. LCMS (10 cm_ESCI_Formic_MeCN): [M+H]+=223 at 3.02 min. 1H NMR (400 MHz, CDCl3): δ 7.86 (s, 1H), 7.53 (s, 1H), 4.40 (s, 2H), 4.02 (s, 3H), 3.24 (s, 3H).

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-84fc1e000b9a48019bafb064aaf4a0d0
Source dataset
uspto-grants-2014_08
Patent number
US08796296B2

Reaction notes

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