Succinic anhydride → HCID 9944511, compound

HRID 2086009Notes

Reaction equation

HRID 2086009 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]2[NH:12][C:11](=[O:16])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]=2[CH:3]=1.[C:17]1(=[O:23])[O:22][C:20](=[O:21])[CH2:19][CH2:18]1>O1CCOCC1>[O:16]=[C:11]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]2[CH:3]=[C:2]([NH:1][C:17](=[O:23])[CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH:15]=[CH:14][C:13]=2[NH:12]1

Participants

4

Reactant 2

HCID 7922Succinic anhydride2×HCID 2706686(5h)-Phenanthridinone, 2-amino-2×

Product 1

HCID 9944511HCID 9944511, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Prepared from 2-amino-6(5H)-phenanthridinone 3 and succinic anhydride. To a solution of 2-amino-6(5H)-phenanthridinone (150 mg, 0.71 mmol) in dioxane (30 mL) was added a solution of succinic anhydride (87 mg, 1.1 mmol) in dioxane (5 mL) over 5 minutes. The mixture was stirred for 16 hours and a yellowish precipitation was formed. Purification of the precipitation by crystallization in dioxane gave a light white solid (92% yield), mp 224-228° C. 1H-NMR (400 MHz DMSO-d6), 11.7 (s, 1H), 10.1 (s, 1H), 8.67 (s, 1H), 8.33 (d, J=7.8 Hz, 1H), 8.24 (d, J=8.2 Hz, 1H), 7.87 (t, J=7.0 Hz, 1H), 7.66 (t, J=7.44 Hz, 1H), 7.60 (t, J=8.7 Hz, 1H),7.30 (d, J=8.7 Hz, 1H), 2.60 ((d, J=5.4 Hz, 2H), 2.56 (d, J=5.4 Hz, 2H). Anal. (C17H24N2O4 .0.1 H2O), C H N.

Workup

  1. customa yellowish precipitation
  2. customwas formed
  3. customPurification of the precipitation
  4. customby crystallization in dioxane

Sources & evidence

ORD record
ord-a4e7de5d00cc412a9220f09c9cfc13e6
Source dataset
uspto-grants-2004_04
Patent number
US06723733B2

Reaction notes

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