Stannous chloride dihydrate → Dibenzyl 5-aminoisophthalate

HRID 581167Notes

Reaction equation

HRID 581167 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[CH:12]=[C:13]([N+:27]([O-])=O)[CH:14]=[C:15]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH:16]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.[Sn](Cl)Cl.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[CH2:1]([O:8][C:9]([C:11]1[CH:12]=[C:13]([CH:14]=[C:15]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH:16]=1)[NH2:27])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 190639261,3-Dibenzyl 5-nitrobenzene-1,3-dicarboxylate

Product 1

HCID 7023592Dibenzyl 5-aminoisophthalateYield 90%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

3,5-dibenzyloxycarbonyl-nitrobenzene (3.91 g, 10 mol) was dissolved in ethyl acetate (50 ml) and tin(II)chloride dihydrate (11.27 g, 50 mmol) was added and the mixture stirred and heated at 70 under an atmosphere of nitrogen for 1 h. The mixture was poured carefully onto 5% sodium hydrogencarbonate solution (200 ml) and a further aliquot of ethyl acetate (100 ml) was added. After shaking the organic layer was separated and the aqueous layer was extracted with more ethyl acetate (50 ml). The combined organic layers were washed with brine, and dried, filtered and evaporated to leave a pale yellow solid (3.25 g, 90%), 1H NMR (CDCl3) δ 8.1 (1H, d), 7.5 (12H, m), 5.4 (4H, s), 3.8 (2H, bs).

Workup

  1. temperatureheated at 70 under an atmosphere of nitrogen for 1 h
  2. stirringAfter shaking the organic layer
  3. customwas separated
  4. extractionthe aqueous layer was extracted with more ethyl acetate (50 ml)
  5. washThe combined organic layers were washed with brine
  6. customdried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-7ef8a3f3ac624f16b74f69112de1650b
Source dataset
uspto-grants-1999_07
Patent number
US05919829

Reaction notes

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