Silica → 2-Methoxy-2'-amino-4,4'-dibromobiphenyl

HRID 565592Notes

Reaction equation

HRID 565592 reaction equation
O.NN.[CH3:4][O:5][C:6]1[CH:11]=[C:10]([Br:12])[CH:9]=[CH:8][C:7]=1[C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:14]=1[N+:20]([O-])=O.O=[Si]=O>C(O)C.[Ru]>[CH3:4][O:5][C:6]1[CH:11]=[C:10]([Br:12])[CH:9]=[CH:8][C:7]=1[C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:14]=1[NH2:20]

Participants

6

Reactant 3

HCID 24261SilicaHCID 24654Hydrazine hydrate (1:1)HCID 99774712-Methoxy-2'-nitro-4,4'-dibromobiphenyl

Product 1

HCID 99984202-Methoxy-2'-amino-4,4'-dibromobiphenylYield 95.46%

Reagents, catalysts & solvents 2

HCID 23950RutheniumCatalystHCID 702EthanolSolvent2×

Conditions

Temperature
67.5 °C

Procedure

A solution of hydrazine hydrate (19.4 mL, 400 mmol) in ethanol (20 mL) was added dropwise into a suspension of 2-methoxy-2′-nitro-4,4′-dibromobiphenyl (15, 25.77 g, 66.59 mmol) and 5% Ru/C (2.69 g, 1.33 mmol) in ethanol (250 mL) maintained at 65-70° C. The reaction mixture was then refluxed for 7 h. The hot reaction mixture was passed through Celite 545 (1 cm thick), and the filtrate was evaporated to give an off-white powder (22.69 g, 95.46%): mp 94.5-97° C.; HPLC method 3 tR=18.57 min (97.9 area %); 1H NMR δ 3.40 (br s, 2 H), 3.80 (s, 3 H), 6.9-7.2 (m, 6 H); EI-MS m/z 355 (M+). Anal. (C13H11ONBr2) C, H, N.

Workup

  1. temperatureThe reaction mixture was then refluxed for 7 h
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-90eb2e2c32834895b89da484fe8b5aa3
Source dataset
uspto-grants-2001_01
Patent number
US06172104B2

Reaction notes

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