Sodium Chloride → HCID 57500699, compound

HRID 1919689Notes

Reaction equation

HRID 1919689 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][N:15]=[CH:16][CH:17]=3)[C:12]3=[CH:19][CH:20]=[CH:21][C:22]([C:23]([NH2:25])=O)=[C:11]3[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[Cl-].[Na+].P(Cl)(Cl)(Cl)=O>ClC(Cl)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][N:15]=[CH:16][CH:17]=3)[C:12]3=[CH:19][CH:20]=[CH:21][C:22]([C:23]#[N:25])=[C:11]3[N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 24813Phosphorus oxychloride2×HCID 57402606HCID 57402606, compound

Product 1

HCID 57500699HCID 57500699, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

5-(3-chlorophenylamino)benzo[c][2,6]naphthyridine-7-carboxamide (12 mg, 0.034 mmol) was suspended in dichloroethane (0.2 ml). Sodium chloride (70 mg) was added followed by Phosphorus oxychloride (20 ul). The mixture was stirred at 80° C. for 1.5 hours. An extra amount of Phosphorus oxychloride (50 ul) was added and the mixture was heated at 80° C. for 8 hours. The volatiles were removed in vacuo. Water was added and the solid was filtered. The material was purified by preparative TLC on silica gel (5% MeOH in CH2Cl2) to provide 6 mg of 5-(3-chlorophenylamino)benzo[c][2,6]naphthyridine-7-carbonitrile. LCMS (ES): >95% pure, m/z 331 [M+1]+.

Workup

  1. temperaturethe mixture was heated at 80° C. for 8 hours
  2. customThe volatiles were removed in vacuo
  3. additionWater was added
  4. filtrationthe solid was filtered
  5. customThe material was purified by preparative TLC on silica gel (5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-dd92cf7ca5574858b52b7c42ddd6ca1e
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

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