Hydrochloric Acid → HCID 12952211, compound

HRID 1577989Notes

Reaction equation

HRID 1577989 reaction equation
Br[C:2]1[CH:15]=[C:14]2[C:5]([O:6][C:7]3[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=3[C:13]2=[O:16])=[CH:4][CH:3]=1.[CH3:17][N:18]1CCCC1=O.Cl>O>[O:16]=[C:13]1[C:14]2[CH:15]=[C:2]([C:17]#[N:18])[CH:3]=[CH:4][C:5]=2[O:6][C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12]1=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 13387N-methyl-2-pyrrolidoneHCID 12952200HCID 12952200, compound

Product 1

HCID 12952211HCID 12952211, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of 252.6 g of 7-bromo-1,2,3,4-tetrahydro-9-xanthone obtained in Example 1, 89.1 g of cuprous cyanide and 900 ml of N-methyl-2-pyrrolidone was heated with stirring for 2 hours at 190° C. and then allowed to cool to 80° C. To the reaction mixture was added a mixture of 300 g of ferric chloride, 450 ml of water and 80 ml of concentrated hydrochloric acid, and the resulting solution was agitated for 30 minutes. After allowing the reaction mixture to stand overnight, the deposited crystals were collected by filtration and washed thoroughly with water. Subsequently, the crystals were dried and recrystallized from acetonitrile to obtain 169.6 g (yield: 83.6%) of 5,6,7,8-tetrahydro-9-oxo-xanthene-2-carbonitrile as brownish prism-like crystals having a melting point of 198° to 200° C.

Workup

  1. temperaturewas heated
  2. temperatureto cool to 80° C
  3. additionTo the reaction mixture was added
  4. stirringthe resulting solution was agitated for 30 minutes
  5. waitto stand overnight
  6. filtrationthe deposited crystals were collected by filtration
  7. washwashed thoroughly with water
  8. customSubsequently, the crystals were dried
  9. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-de3a8d94f9bb4e71971382bdd5721dc3
Source dataset
uspto-grants-1981_09
Patent number
US04290954

Reaction notes

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