HCID 22667729, compound → HCID 22667746, compound

HRID 844125Notes

Reaction equation

HRID 844125 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:16]([O-])=O)=[C:6]([N:8]([CH2:12][C:13](O)=[O:14])[CH:9]([CH3:11])[CH3:10])[CH:7]=1>C(O)(=O)C.[Fe]>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:16][C:13](=[O:14])[CH2:12][N:8]2[CH:9]([CH3:11])[CH3:10]

Participants

4

Reactant 1

HCID 22667729HCID 22667729, compound

Product 1

HCID 22667746HCID 22667746, compoundYield 73.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of [(5-bromo-2-nitro-phenyl)-isopropyl-amino]acetic acid (27 g, 85 mmol) in acetic acid (400 ml) was added iron powder (15 g, 0.27 mol) and the mixture was stirred for 2 hrs. at 90° C. The reaction mixture was cooled, filtered, and the acetic acid was evaporated. The remaining slurry was extracted with CH2Cl2 (3×300 ml). The CH2Cl2 extracts were combined, dried (MgSO4) and evaporated to afford the subtitled compound (16.8 g, 73%): 1H-NMR (DMSO-d6) δ1.13 (d, J=6.54 Hz, 6H), 3.57 (s, 2H), 3.99 (septet, J=6.54 Hz, 1H), 6.82 (dd, J=8.23, 1.88 Hz, 1H), 6.72 (d, J=8.17 Hz, 1H), 6.90 (d, J=1.59 Hz, 1H), 10.50 (s, 1H): MS (EI) 267/269 (M)++1 bromine.

Workup

  1. customat 90° C
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. customthe acetic acid was evaporated
  5. extractionThe remaining slurry was extracted with CH2Cl2 (3×300 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-306f052d910d4f558dbacb6609f9a016
Source dataset
uspto-grants-2002_04
Patent number
US06380235B1

Reaction notes

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