Water → HCID 22105528, compound

HRID 1455978Notes

Reaction equation

HRID 1455978 reaction equation
[CH2:1]([O:8][C:9]1[CH:30]=[CH:29][C:28]([Br:31])=[CH:27][C:10]=1[CH2:11][NH:12][C:13]1[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][C:14]=1[N+:24]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O>C(O)(=O)C.[Fe]>[CH2:1]([O:8][C:9]1[CH:30]=[CH:29][C:28]([Br:31])=[CH:27][C:10]=1[CH2:11][NH:12][C:13]1[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][C:14]=1[NH2:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 962Water2×HCID 22105604HCID 22105604, compound

Product 1

HCID 22105528HCID 22105528, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

Ethyl 4-[N-(2-benzyloxy-5-bromobenzyl)amino]3-nitrobenzoate (10 g) was dissolved in acetic acid (50 mL) (warming was required) and iron dust (6.92 g) was added followed by the addition of water (20 mL). There was an exothermic reaction (to 70° C.). The reaction mixture was stirred at ambient temperature for 16 hours, water (300 mL) was added and the mixture was extracted three times with ethyl acetate (100 mL each time). The combined extracts were washed consecutively with water (3×100 mL) and saturated aqueous sodium bicarbonate (2×100 mL) and dried (MgSO4). The residue obtained on removal of the solvent was filtered through silica, eluting initially with a mixture of dichloromethane and hexane (1/1 v/v) and then with dichloromethane, to give ethyl 4-[N-(2-benzyloxy-5-bromobenzyl)amino]-3-aminobenzoate, yield 8.78 g, mp 135° C.

Workup

  1. customan exothermic reaction (to 70° C.)
  2. extractionthe mixture was extracted three times with ethyl acetate (100 mL each time)
  3. washThe combined extracts were washed consecutively with water (3×100 mL) and saturated aqueous sodium bicarbonate (2×100 mL)
  4. dry with materialdried (MgSO4)
  5. customThe residue obtained on removal of the solvent
  6. filtrationwas filtered through silica
  7. washeluting initially with a mixture of dichloromethane and hexane (1/1 v/v)

Sources & evidence

ORD record
ord-fd4b6a2446f445e7ace2098c0117cad6
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Reaction notes

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