Water → HCID 54693166, compound

HRID 1244091Notes

Reaction equation

HRID 1244091 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:18]3[C:17]([OH:19])=[C:16]([C:20]#[N:21])[C:15](=[O:22])[NH:14][C:13]=3[S:12][CH:11]=2)=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+].O>C(O)C.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:18]3[C:17]([OH:19])=[C:16]([C:20]#[N:21])[C:15](=[O:22])[NH:14][C:13]=3[S:12][CH:11]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 54708525HCID 54708525, compound

Product 1

HCID 54693166HCID 54693166, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a stirred suspension of 3-(4-nitrophenyl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile (0.054 g, 0.173 mmol) and ammonium chloride (0.007 g, 0.138 mmol) in ethanol: water mixture (2:1, 24 mL) was added iron powder (0.097 g, 1.73 mmol) in a single portion. The reaction mixture was heated at reflux for 16 hours, cooled to room temperature, filtered and the filtrate concentrated under reduced pressure. The residue was taken up in DMSO/MeOH and purified by RP-HPLC. MS (ESI) m/e 281.7 (M−H)+; 1H NMR (400 MHz, DMSO-d6): δ ppm 11.65 (br s, 1H), 7.31 (d, 2H), 6.88 (d, 2H), 6.74 (s, 1H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 16 hours
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under reduced pressure
  5. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-3d4b4144f1614152aa98f80f7128643b
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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