Ammonium Chloride → HCID 69964118, compound

HRID 2288575Notes

Reaction equation

HRID 2288575 reaction equation
[Cl-].[NH4+].[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]2[C:17]([CH:18]=1)=[N:16][C:15]1[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:9]=2[C:19]([O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:20]>C(O)C.C(OCC)(=O)C.[Zn]>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]2[CH:9]([C:19]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:20])[C:10]3[C:15]([NH:16][C:17]=2[CH:18]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 18006778HCID 18006778, compound

Product 1

HCID 69964118HCID 69964118, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ammonium chloride (3.45 g, 64 mmol) and 4.2 g of zinc (64 mmol) were added to an Ar-purged suspension of 0.85 g (2.5 mmol) of the ester from step (c) in 50 mL of 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 used without further purification. 1H NMR (CDCl3) δ 3.76 (s, 3H), 5.29 (s, 1H), 6.47-7.36 (m, 12H), 8.21 (br s, 1H).

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 used without further purification

Sources & evidence

ORD record
ord-b31d7a51c23f4270b429065a1ba073a9
Source dataset
uspto-grants-2000_07
Patent number
US06090571

Reaction notes

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