Phthalic Anhydride → HCID 68860277, compound

HRID 898864Notes

Reaction equation

HRID 898864 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH2:11][CH:10]([NH2:15])[CH2:9][CH2:8]2.[C:16]1(=O)[O:21][C:19](=[O:20])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12>CN(C=O)C.O>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH2:11][CH:10]([N:15]1[C:19](=[O:20])[C:18]3[C:17](=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:16]1=[O:21])[CH2:9][CH2:8]2

Participants

6

Reactant 3

HCID 6811Phthalic AnhydrideHCID 199076-Methoxy-1,2,3,4-tetrahydro-naphthalen-2-ylamineHCID 24758Sodium hydride

Product 1

HCID 68860277HCID 68860277, compoundYield 68.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of 60% NaH (6 g; 0.182 mmol) in DMF (400 mL) is added 6-methoxy-1,2,3,4-tetrahydronaphthalen-2-ylamine (30 g; 0.140 mol), portionwise at 0° C. The reaction mixture is warmed to RT and stirred for an additional 1 h. Phthalic anhydride (20.7 g; 0.139 mol) is added in 1-portion at RT, upon which the reaction mixture is stirred for an additional 1 h followed by 18 h at 120° C. The reaction was allowed to cool to RT, diluted with H2O and extracted several times with EtOAc. The combined organic extracts are washed with water, brine, dried over Na2SO4, and the solvent removed under reduced pressure. The crude solid was triturated with MeOH, filtered, and dried under vacuo to afford 29.1 g (67%) of 2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)isoindole-1,3-dione as an off-white solid.

Workup

  1. customportionwise at 0° C
  2. stirringupon which the reaction mixture is stirred for an additional 1 h
  3. waitfollowed by 18 h at 120° C
  4. temperatureto cool to RT
  5. extractionextracted several times with EtOAc
  6. washThe combined organic extracts are washed with water, brine
  7. dry with materialdried over Na2SO4
  8. customthe solvent removed under reduced pressure
  9. customThe crude solid was triturated with MeOH
  10. filtrationfiltered
  11. customdried under vacuo

Sources & evidence

ORD record
ord-b1b1214b17aa41e9ab75776c848cc32f
Source dataset
uspto-grants-2008_04
Patent number
US07351857B2

Reaction notes

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