4-Tert-Butylaniline → HCID 69034326, compound

HRID 2251834Notes

Reaction equation

HRID 2251834 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:4]=1[C:5]([O:7]C)=O.[C:16]([C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17].CCN(C(C)C)C(C)C>CC(O)(C)C>[C:16]([C:20]1[CH:21]=[CH:22][C:23]([N:24]2[CH2:2][C:3]3[C:4](=[C:9]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:11][CH:12]=3)[C:5]2=[O:7])=[CH:25][CH:26]=1)([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 698614-Tert-ButylanilineHCID 81531DiisopropylethylamineHCID 21708527Methyl 2-(bromomethyl)-6-nitrobenzoate

Product 1

HCID 69034326HCID 69034326, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of methyl 2-bromomethyl-6-nitro-benzoate (0.73 mmol, 1 eq.) and t-BuOH (3 mL) in a sealed reaction vial was added 4-t-butylaniline (0.73 mmol, 1 eq) and DIEA (0.38 mL, 3 eq). The reaction was stirred at RT for 30 min then heated at 170° C. for 10 min in a microwave. A yellow solid was filtered and washed with t-BuOH and H2O then dried under high-vacuum to afford 2-(4-tert-butyl-phenyl)-7-nitro-2,3-dihydro-isoindol-1-one. MS m/e 311 (M+H)+.

Workup

  1. temperaturethen heated at 170° C. for 10 min in a microwave
  2. filtrationA yellow solid was filtered
  3. washwashed with t-BuOH and H2O
  4. customthen dried under high-vacuum

Sources & evidence

ORD record
ord-84b6eb94deb44a879097a87522411783
Source dataset
uspto-grants-2008_01
Patent number
US07320992B2

Reaction notes

Loading…