Ammonium Chloride → 2-Bromo-3-methylaniline

HRID 723050Notes

Reaction equation

HRID 723050 reaction equation
[Br:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:11].[Cl-].[NH4+]>[Fe]>[Br:1][C:2]1[C:3]([CH3:11])=[CH:4][CH:5]=[CH:6][C:7]=1[NH2:8]

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 2318282-Bromo-3-nitrotoluene

Product 1

HCID 6037812-Bromo-3-methylaniline

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

The procedure as in Example 20: step c was followed using 2-bromo-1-methyl-3-nitro-benzene (1 g, 4.6 mmol dissolved in 12 mL EtOH, Aldrich Chemical Company), ammonium chloride (2.5 g, 46 mmol dissolved in 6 mL H2O) and iron (1.3 g, 23 mmol). The title compound was obtained (1.0 g, quantitative yield) which was used without further purification. 1H-NMR (CDCl3): δ 6.95–7.00 (t, 1H, J=7.6 Hz), 6.60–6.65 (dd, 2H, J=8.1, 4.4 Hz), 4.10 (br s, 2H), 2.35 (s, 3H).

Sources & evidence

ORD record
ord-df124ce09467468baa5900ab178e7672
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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