Water → HCID 69367776, compound

HRID 1351746Notes

Reaction equation

HRID 1351746 reaction equation
[CH2:1]([O:8][C:9](=[O:21])[C:10]1[CH:15]=[C:14]([Br:16])[CH:13]=[C:12]([N+:17]([O-])=O)[C:11]=1[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH4+].[Cl-]>CCOC(C)=O.[Fe]>[CH2:1]([O:8][C:9](=[O:21])[C:10]1[CH:15]=[C:14]([Br:16])[CH:13]=[C:12]([NH2:17])[C:11]=1[CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 69367116Benzyl 5-bromo-2-methyl-3-nitrobenzoate

Product 1

HCID 69367776HCID 69367776, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A 1000 mL RBF equipped with an overhead stirrer was charged with 5-bromo-2-methyl-3-nitro benzoic acid benzyl ester (75.0 g, 0.214 mol) and water (200 mL). While stirring vigorously, Fe powder (−325 mesh, 47.81 g, 0.857 mol) and NH4Cl (13.88 g, 0.257 mol) were added. The mixture was heated to reflux for 4.5 hours. The reaction mixture was then allowed to cool to room temperature, diluted with EtOAc and filtered through a pad of Celite. The filtrate was washed with water (2×), saturated NaCl (1×), dried (MgSO4), and concentrated. Upon trituration with hexanes, 63.2 g (92.1%) of an off-white powder was obtained. 1H NMR (CDCl3) δ 7.38 (m, 6H), 6.90 (s, 1H), 5.31 (s, 2H), 3.76 (br s, 2H), 2.25 (s, 3H).

Workup

  1. customA 1000 mL RBF equipped with an overhead stirrer
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 4.5 hours
  4. filtrationfiltered through a pad of Celite
  5. washThe filtrate was washed with water (2×), saturated NaCl (1×)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-499f3d4f918543a7935491db85e7546c
Source dataset
uspto-grants-2007_05
Patent number
US07217730B2

Reaction notes

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