Sodium Chloride → HCID 22672699, compound

HRID 53179Notes

Reaction equation

HRID 53179 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 eq.) of t-butyl 4-(acetoxymethyl)-3-nitrobenzoate in MeOH (200 mL) was added 27.0 mL (477 mmol, 10.0 eq.) 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. The reaction is represented in Scheme 5.

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-8696268071ea45348e7d15bd2e5705cc
Source dataset
uspto-grants-1997_04
Patent number
US05618825

Reaction notes

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