Ethanol → HCID 22348058, compound

HRID 897246Notes

Reaction equation

HRID 897246 reaction equation
[Cl-].[NH4+].[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([CH2:12][N:13]3[CH2:18][CH2:17][CH:16]([NH:19][C:20]4[C:29]5[C:24](=[CH:25][CH:26]=[C:27]([Cl:30])[CH:28]=5)[O:23][C:22](=[O:31])[C:21]=4[N+:32]([O-])=O)[CH2:15][CH2:14]3)=[CH:11][C:6]=2[O:5][CH2:4]1.[CH2:35]([OH:37])[CH3:36]>O.[Fe]>[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([CH2:12][N:13]3[CH2:18][CH2:17][CH:16]([NH:19][C:20]4[C:29]5[C:24](=[CH:25][CH:26]=[C:27]([Cl:30])[CH:28]=5)[O:23][C:22](=[O:31])[C:21]=4[NH:32][C:35](=[O:37])[CH3:36])[CH2:15][CH2:14]3)=[CH:11][C:6]=2[O:5][CH2:4]1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 22348177HCID 22348177, compound

Product 1

HCID 22348058HCID 22348058, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

Iron powder (0.067 g, 1.2 mmol) was added to a suspension of ammonium chloride (0.006 g, 0.12 mmol) and 4-(1-Benzo[1.3]dioxol-5-ylmethyl-piperidin-4-ylamino)-6-chloro-3-nitro-chromen-2-one (0.055 g, 0.12 mmol) in ethanol (5 mL) and water (2 mL) at room temperature. The reaction was heated at reflux for 1 d and then filtered through a pad of wet celite. The filtrate was treated with saturated NaHCO3 (10 mL), extracted with dichloromethane (3×25 mL), dried (Na2SO4), concentrated, purified by RP-HPLC and the amine carried forward to the next step. MS (ESI) m/e 428.0 (M+H)+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 1 d
  3. filtrationfiltered through a pad of wet celite
  4. additionThe filtrate was treated with saturated NaHCO3 (10 mL)
  5. extractionextracted with dichloromethane (3×25 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-aa4e32689ce54181bed65096a90f7e06
Source dataset
uspto-grants-2005_07
Patent number
US06921821B2

Reaction notes

Loading…