Ammonium Chloride → HCID 69965558, compound

HRID 2288577Notes

Reaction equation

HRID 2288577 reaction equation
[Cl-].[NH4+].[CH:3]1[C:20]2[C:19]3[C:10](=[C:11]([C:21]([O:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[O:22])[C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=4[N:18]=3)[CH:9]=[CH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1>C(O)C.C(OCC)(=O)C.[Zn]>[CH:3]1[C:20]2[C:19]3[NH:18][C:17]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[CH:11]([C:21]([O:23][C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)=[O:22])[C:10]=3[CH:9]=[CH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 18006808HCID 18006808, compound

Product 1

HCID 69965558HCID 69965558, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ammonium chloride (10 g) and 10 g of zinc were added to an Ar-purged suspension of 1.0 g of the ester from step (b) in ethanol. The mixture was stirred for 2 h, filtered and the solids washed with CH2Cl2. The combined solutions were evaporated to dryness producing a white solid which was dissolved in ethyl acetate and washed with 3×25 mL of water. The product was purified by chromatography using 10% ethyl acetate/hexane. 1H NMR (CDCl3) δ 5.48 (s, 1H), 5.69-7.27 (m, 9H), 7.41-7.55 (m, 5H), 7.83-7.88 (m, 2H).

Workup

  1. filtrationfiltered
  2. washthe solids washed with CH2Cl2
  3. customThe combined solutions were evaporated to dryness
  4. customproducing a white solid which
  5. washwashed with 3×25 mL of water
  6. customThe product was purified by chromatography

Sources & evidence

ORD record
ord-4be2b2de4ff445d1b037550fbd914cf5
Source dataset
uspto-grants-2000_07
Patent number
US06090571

Reaction notes

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