Water → 2-(1,1-dimethyl-2-hydroxyethyl)-5-nitro-2,3-dihydro-1H-isoindol

HRID 9724

Reaction equation

HRID 9724 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=O)O[C:8](=O)[C:7]2=[CH:13][CH:14]=1)([O-:3])=[O:2].[NH2:15][C:16]([CH3:20])([CH3:19])[CH2:17][OH:18].O>C(Cl)Cl>[CH3:19][C:16]([N:15]1[CH2:11][C:6]2[C:7](=[CH:13][CH:14]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH2:8]1)([CH3:20])[CH2:17][OH:18]

Participants

5

Reactant 3

HCID 962WaterHCID 118072-Amino-2-methyl-1-propanolHCID 2309764-Nitrophthalic acid anhydride

Product 1

HCID 219881562-(1,1-dimethyl-2-hydroxyethyl)-5-nitro-2,3-dihydro-1H-isoindol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

20 g of 4-Nitro-phthalic anhydride and 8.94 g of 2-amino-2-methylpropanol were heated to 170° C. for 30 min. After cooling, water and CH2Cl2 were added, and the organic phase separated, concentrated and purified by chromatography on silica (eluent CH2Cl2/MeOH 97/3).

Workup

  1. temperatureAfter cooling
  2. customthe organic phase separated
  3. concentrationconcentrated
  4. custompurified by chromatography on silica (eluent CH2Cl2/MeOH 97/3)

Sources & evidence

ORD record
ord-a28dfc986e8549b3bda0a7e2c9a0bc50
Source dataset
uspto-grants-2006_08
Patent number
US07091345B2

Linked notes

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