HCID 23560772, compound → HCID 23560799, compound

HRID 1058387Notes

Reaction equation

HRID 1058387 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-])=O)[CH:15]=2)=[O:11])=[CH:6][C:5]=1[Br:23]>O.C(O)(=O)C.[Fe]>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[CH:15]=2)=[O:11])=[CH:6][C:5]=1[Br:23]

Participants

5

Reactant 1

HCID 23560772HCID 23560772, compound

Product 1

HCID 23560799HCID 23560799, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
25 °C

Procedure

Iron powder (135 mg, 2.4 mmol) was added to a suspension of 2-bromo-4-[[(3-nitrobenzyl)amino]carbonyl]benzoic acid methyl ester (Example 85; 125 mg, 3.18 mmol) in water (530 μL) and acetic acid (111 μL) at 25° C. The reaction was heated to reflux for 30 min and then cooled to 25° C. The suspension was diluted with water (20 mL), stirred 15 min, filtered over Celite® and washed well with water (100 mL). The filtrate was washed with ethyl acetate (50 mL) followed by ethyl acetate containing 2% methanol (50 mL). The organic layers were combined, dried (MgSO4), filtered and concentrated. The residue was diluted with 10% methanol in dichloromethane and stirred with Celite®. After 1 h, the suspension was filtered and washed well with 10% methanol in dichloromethane and the combined filtrates were evaporated to dryness to give 2-bromo-4-[[(3-aminobenzyl)amino]carbonyl]benzoic acid methyl ester (100 mg, 87% yield) as an off-white solid.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 30 min
  3. filtrationfiltered over Celite®
  4. washwashed well with water (100 mL)
  5. washThe filtrate was washed with ethyl acetate (50 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. additionThe residue was diluted with 10% methanol in dichloromethane
  10. stirringstirred with Celite®
  11. waitAfter 1 h
  12. filtrationthe suspension was filtered
  13. washwashed well with 10% methanol in dichloromethane
  14. customthe combined filtrates were evaporated to dryness

Sources & evidence

ORD record
ord-fd3e1cf6055c427880a1544a90b757d8
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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