Diethyl Ether → Dibenzyl 5-aminoisophthalate

HRID 889841Notes

Reaction equation

HRID 889841 reaction equation
[CH2:1]([O:8][C:9](=[O:29])[C:10]1[CH:25]=[C:24]([N+:26]([O-])=O)[CH:23]=[C:12]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCOCC>C(O)(=O)C.[Zn]>[CH2:16]([O:15][C:13](=[O:14])[C:12]1[CH:23]=[C:24]([NH2:26])[CH:25]=[C:10]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:29])[CH:11]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 190639261,3-Dibenzyl 5-nitrobenzene-1,3-dicarboxylate

Product 1

HCID 7023592Dibenzyl 5-aminoisophthalateYield 22%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

In acetic acid (15 mL) was stirred 5-nitroisophthalic acid dibenzyl ester (1.3 g, 3.3 mmol). To this was added in parts zinc dust (1.75 g, 26.6 mmol). The mixture was stirred at room temperature for 18 hours. The mixture was filtered free of insoluble material and the acetic acid solution evaporated at reduced pressure. This residue was dissolved in ethyl acetate (120 mL) and washed successively with saturated sodium bicarbonate solution (50 mL), water (50 mL), and brine (50 mL). The organic phase was dried over magnesium sulfate and evaporated in vacuo to give a solid. The solid was stirred into ether (75 mL) and brought to reflux. The solution allowed to recrystallize to give 260 mg (22%) of a white solid. MS: M+1=362.2.

Workup

  1. filtrationThe mixture was filtered free of insoluble material
  2. customthe acetic acid solution evaporated at reduced pressure
  3. dissolutionThis residue was dissolved in ethyl acetate (120 mL)
  4. washwashed successively with saturated sodium bicarbonate solution (50 mL), water (50 mL), and brine (50 mL)
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. customevaporated in vacuo
  7. customto give a solid
  8. temperatureto reflux
  9. customto recrystallize

Sources & evidence

ORD record
ord-733def17de0f4c6ea64fa843d7cb3d57
Source dataset
uspto-grants-2006_02
Patent number
US06995151B2

Reaction notes

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