Phosphorus oxychloride → HCID 21445446, compound

HRID 597562Notes

Reaction equation

HRID 597562 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=O)[C:6]1[NH:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[C:5]2=1.P(Cl)(Cl)([Cl:22])=O>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([Cl:22])[C:6]1[NH:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[C:5]2=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 21445447HCID 21445447, compound

Product 1

HCID 21445446HCID 21445446, compound

Procedure

A suspension of 60 g. of 2-chloro-7H-indolo[2,3-c]quinolin-6(5H)-one in 950 ml. of phosphorous oxychloride was heated under nitrogen on a steam bath for 2 hours. The deep yellow granular complex that formed was collected and washed thoroughly with anhydrous ether (85.5 g.). After drying, this complex was suspended in 500 ml. of water to which 300 ml. of concentrated aqueous ammonium hydroxide solution was added, in portions, with stirring. The resulting pale yellow solid was collected and washed with water. After recrystallization from 2 l. of acetonitrile, 37.5 g. (68 percent) of colorless needles of 2,6-dichloro-7H-indolo[2,3-c]quinoline was obtained, which had a melting point of 262°-264°. sample, melting point 265°-266°.

Workup

  1. additionA suspension of 60 g
  2. customThe deep yellow granular complex that formed
  3. customwas collected
  4. washwashed thoroughly with anhydrous ether (85.5 g.)
  5. customAfter drying
  6. additionof concentrated aqueous ammonium hydroxide solution was added, in portions
  7. customThe resulting pale yellow solid was collected
  8. washwashed with water
  9. customAfter recrystallization from 2 l

Sources & evidence

ORD record
ord-3b93aa4f3ef94b719369e7c6b6ecc281
Source dataset
uspto-grants-1977_03
Patent number
US04014883

Reaction notes

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