Ethanol → HCID 57842769, compound

HRID 735671Notes

Reaction equation

HRID 735671 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C@H:10]([NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:11])[CH:7]=[CH:8][CH:9]=1)([O-])=O.CCO.O>[Fe].CC(O)=O>[NH2:1][C:4]1[CH:5]=[C:6]([C@H:10]([NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH3:11])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 962WaterHCID 57842840HCID 57842840, compound

Product 1

HCID 57842769HCID 57842769, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a refluxing solution of 64A (5 g, 16.7 mmol), EtOH (100 mL), water (30 mL) and AcOH (15 mL) was added portion-wise Fe powder (5 g, 89 mmol) over 30 min. The mixture was heated for 1 h. before cooling to ambient temperature. and filtering through celite. The filtrate was concentrated in vacuo to afford 64B (2.7 g, 61%) as an oil. MS (ESI) m/z 271.2 (M+H)+.

Workup

  1. temperatureThe mixture was heated for 1 h.
  2. filtrationand filtering through celite
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-dcdfb021cefd4e79914f9f77133396a6
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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