Hydrogen Peroxide → HCID 50941656, compound

HRID 1919648Notes

Reaction equation

HRID 1919648 reaction equation
[C:1]1([NH:7][C:8]2[C:17]3[CH:18]=[CH:19][S:20][C:16]=3[C:15]3[CH:14]=[CH:13][C:12]([C:21]#[N:22])=[CH:11][C:10]=3[N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:23]O.[OH-].[Na+].O>CN1C(=O)CCC1>[C:1]1([NH:7][C:8]2[C:17]3[CH:18]=[CH:19][S:20][C:16]=3[C:15]3[CH:14]=[CH:13][C:12]([C:21]([NH2:22])=[O:23])=[CH:11][C:10]=3[N:9]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 784Hydrogen Peroxide2×HCID 962WaterHCID 14798Sodium Hydroxide2×HCID 50941655HCID 50941655, compound

Product 1

HCID 50941656HCID 50941656, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
50 °C

Procedure

4-(phenylamino)thieno[3,2-c]quinoline-7-carbonitrile (34 mg, 0.113 mmol) was dissolved in NMP (0.3 ml). 30% aqueous H2O2 (0.2 ml) was added followed by addition of 6N NaOH (50 ul). The mixture was stirred at 50° C. for 2 hours. An extra amount of 30% aqueous H2O2 (0.3 ml) and 6N NaOH (100 ul) were added and a 70% conversion was achieved after 30 min. Water was added and the solid filtered and dried. The material was further reacted under the same conditions in order to achieve a complete transformation. 4-(phenylamino)thieno[3,2-c]quinoline-7-carboxamide was isolated as solid (30 mg, 83% yield). LCMS (ES): 95% pure, m/z 320 [M+1]+.

Workup

  1. waita 70% conversion was achieved after 30 min
  2. filtrationthe solid filtered
  3. customdried
  4. customThe material was further reacted under the same conditions in order

Sources & evidence

ORD record
ord-a29f4938f7af4a00950c5dd311748fdc
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

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