Water → HCID 44380045, compound

HRID 344010Notes

Reaction equation

HRID 344010 reaction equation
[N+]([C:4]1[CH:17]=[CH:16][C:15]2[C:14](=[O:18])[C:13]3[C:8](=[C:9]([C:19](=[O:21])[CH3:20])[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:22])[C:6]=2[C:5]=1[C:23](=[O:25])[CH3:24])([O-])=O.[O:26]1[CH2:30]CCC1.[C-]#N.[Na+].[OH2:34]>>[C:30]([C:17]1[CH:4]=[C:5]([C:23](=[O:25])[CH3:24])[C:6]2[C:7](=[O:22])[C:8]3[C:13]([C:14](=[O:18])[C:15]=2[CH:16]=1)=[CH:12][CH:11]=[CH:10][C:9]=3[C:19](=[O:21])[CH3:20])([OH:26])=[O:34]

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 8929Sodium CyanideHCID 53826450HCID 53826450, compound

Product 1

HCID 44380045HCID 44380045, compoundYield 44%

Conditions

Temperature
50 °C

Procedure

Mono-nitro 1,8-diacetylanthraquinone (1 g; M.W. 397; 2.52 mmoles) was added to 10 ml of a mixture tetrahydrofuran: water=20:80 by volume. The mixture was heated to 50° C. under constant stirring followed by addition of NaCN (1.4 g; M.W. 49; 28.57 moles). The reaction mixture was maintained overnight at 50° C. under constant agitation. The resulting mixture was filtered and washed with water. The bright yellow-greenish crystals were dried at 50° C. 3-carboxy-1,8-diacetylanthraquinone was obtained in a 44% yield.

Workup

  1. temperatureThe reaction mixture was maintained overnight at 50° C. under constant agitation
  2. filtrationThe resulting mixture was filtered
  3. washwashed with water
  4. customThe bright yellow-greenish crystals were dried at 50° C

Sources & evidence

ORD record
ord-cb836807e47542b4a1d9b6955da4da88
Source dataset
uspto-grants-1999_01
Patent number
US05864048

Reaction notes

Loading…