Ammonium Chloride → HCID 86737785, compound

HRID 1680225Notes

Reaction equation

HRID 1680225 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C@H:8]3[N:20]([CH3:21])[CH2:19][CH2:18][C@:14]45[C:15]=2[C:16]=1[O:17][CH:13]4[C:12](=[O:22])[CH2:11][CH2:10][C@@:9]35[O:23][CH3:24].[Cl-:25].[NH4+]>[Zn].C(O)C>[ClH:25].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C@H:8]3[N:20]([CH3:21])[CH2:19][CH2:18][C@@:14]4([C:15]=2[C:16]=1[OH:17])[C@@:9]3([O:23][CH3:24])[CH2:10][CH2:11][C:12](=[O:22])[CH2:13]4

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 57235184HCID 57235184, compound

Product 1

HCID 86737785HCID 86737785, compoundYield 145.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

A mixture of 15 (1.67 g), Zn dust (0.72 g), ammonium chloride (1.1 g) and ethanol (45 ml) was refluxed for 6 hour under N2 atmosphere. The product was filtered and the residual solid washed with ethanol. The filtrate was concentrated under reduced pressure to give the hydrochloride salt of 16 as a white solid (2.71 g). This product contained some ammonium chloride but was used without purification in the next reaction. Attempts to purify the material by preparation of the free base resulted in loss of material.

Workup

  1. temperaturewas refluxed for 6 hour under N2 atmosphere
  2. filtrationThe product was filtered
  3. washthe residual solid washed with ethanol
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-db9c383a403840d9bda53ddb9686642c
Source dataset
uspto-grants-1981_06
Patent number
US04272540

Reaction notes

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