Water → 6-Nitro-2-(phenylmethyl)-1,3(2H,4H)-isoquinolinedione

HRID 1954425Notes

Reaction equation

HRID 1954425 reaction equation
[C:1]([CH2:4][C:5]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=O)([OH:3])=O.[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>C(O)(=O)C>[CH2:17]([N:24]1[C:1](=[O:3])[CH2:4][C:5]2[C:6](=[CH:10][CH:11]=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=2)[C:7]1=[O:9])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7504BenzylamineHCID 71720252-(Carboxymethyl)-4-nitrobenzoic acid

Product 1

HCID 232961796-Nitro-2-(phenylmethyl)-1,3(2H,4H)-isoquinolinedione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
115 °C

Procedure

To a suspension of the diacid (9) (55 g, 0.244 mole) in acetic acid (550 mL) was added benzylamine (28.91 g, 0.27 mole). The reaction was heated to 115° C. for 18 hrs., cooled to 25° C., water was added (450 mL), the contents stirred for 2 hrs., and the product filtered off as a white solid. The product was washed with water (400 mL) and vacuum dried to give 59.51 g (82%).

Workup

  1. temperature, cooled to 25° C.
  2. filtration, and the product filtered off as a white solid
  3. washThe product was washed with water (400 mL) and vacuum
  4. customdried
  5. customto give 59.51 g (82%)

Sources & evidence

ORD record
ord-7076836b7d50455dbee75a7b54d10223
Source dataset
uspto-grants-2000_09
Patent number
US06121283

Reaction notes

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