Hydrochloric Acid → 2-{4-[ethyl(2-hydroxyethyl)amino]phenyl}-6-nitro-1H-benzo[de]isoquinolin-1,3(2H)-dione

HRID 1983964Notes

Reaction equation

HRID 1983964 reaction equation
[N+:1]([C:4]1[C:13]2[C:8]3=[C:9]([C:14]([O:16][C:17](=[O:18])[C:7]3=[CH:6][CH:5]=1)=O)[CH:10]=[CH:11][CH:12]=2)([O-:3])=[O:2].O.S(O)(O)(=O)=O.[CH2:25]([N:27]([CH2:35][CH2:36][OH:37])[C:28]1[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][CH:29]=1)[CH3:26].Cl>N1C=CN=C1>[CH2:25]([N:27]([CH2:35][CH2:36][OH:37])[C:28]1[CH:33]=[CH:32][C:31]([N:34]2[C:17](=[O:18])[C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[C:13]4[C:8]=3[C:9](=[CH:10][CH:11]=[CH:12]4)[C:14]2=[O:16])=[CH:30][CH:29]=1)[CH3:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 811504-Nitro-1,8-naphthalic anhydrideHCID 20189862N-ethyl-N-(2-hydroxyethyl)-p-phenylenediamine sulfate monohydrate

Product 1

HCID 866134062-{4-[ethyl(2-hydroxyethyl)amino]phenyl}-6-nitro-1H-benzo[de]isoquinolin-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 795ImidazoleSolvent

Procedure

2.0 g (8.22 mmol) of 4-nitronaphthalene-1,8-dicarboxylic anhydride and 2.68 g (9.04 mmol) of N-ethyl-N-(2-hydroxyethyl)-p-phenylenediamine sulfate monohydrate were stirred in 12 g of molten imidazole at 130° C. under an argon atmosphere for 1 hour. After cooling, the mixture was poured into 400 mL of 2 N hydrochloric acid and the precipitate was suction-filtered off, washed with water and dried. The resulting product was used in Step 2 without further purification.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate was suction-filtered off
  3. washwashed with water
  4. customdried
  5. customThe resulting product was used in Step 2 without further purification

Sources & evidence

ORD record
ord-af8281ffb2db4133af0792afd2f8cd30
Source dataset
uspto-grants-2009_06
Patent number
US07544215B2

Reaction notes

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