Sodium Chloride → HCID 22672699, compound

HRID 1006646Notes

Reaction equation

HRID 1006646 reaction equation
C([O:4][CH2:5][C:6]1[CH:18]=[CH:17][C:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:8][C:7]=1[N+:19]([O-:21])=[O:20])(=O)C.O.NN.CCOC(C)=O.[Na+].[Cl-]>CO>[OH:4][CH2:5][C:6]1[CH:18]=[CH:17][C:9]([C:10]([O:12][C:13]([CH3:16])([CH3:14])[CH3:15])=[O:11])=[CH:8][C:7]=1[N+:19]([O-:21])=[O:20]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8857Ethyl AcetateHCID 24654Hydrazine hydrate (1:1)HCID 22672701HCID 22672701, compound

Product 1

HCID 22672699HCID 22672699, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 14.1 g (47.7 mmol, 1.00 equiv.) of t-butyl 4-(acetoxymethyl)-3-nitrobenzoate in MeOH (200 mL) was added 27.0 mL (477 mmol, 10.0 equiv.) of hydrazine hydrate (55% hydrazine). The resulting yellow solution was stirred at 25° C. for 4 hr. EtOAc (250 mL) and saturated aq. NaCl (85 mL) were added, and the organic layer collected after shaking. The organic layer was washed further with saturated aq. NaCl (2×85 mL), and then dried (MgSO4). Removal of volatiles in vacuo gave the product in 93% yield as yellow crystals.

Workup

  1. customthe organic layer collected
  2. stirringafter shaking
  3. washThe organic layer was washed further with saturated aq. NaCl (2×85 mL)
  4. dry with materialdried (MgSO4)
  5. customRemoval of volatiles in vacuo
  6. customgave the product in 93% yield as yellow crystals

Sources & evidence

ORD record
ord-d8c7ba8e851d44c4b4e6a434a1003be0
Source dataset
uspto-grants-2004_09
Patent number
US06790965B1

Reaction notes

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