4-(p-Tolyloxy)aniline → HCID 68512931, compound

HRID 1716294Notes

Reaction equation

HRID 1716294 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=O)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[C:12]1([CH3:26])[CH:17]=[CH:16][C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=2)=[CH:14][CH:13]=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][NH:25][C:22]2[CH:21]=[CH:20][C:19]([O:18][C:15]3[CH:16]=[CH:17][C:12]([CH3:26])=[CH:13][CH:14]=3)=[CH:24][CH:23]=2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 945194-(p-Tolyloxy)anilineHCID 15164035-Bromo-2-methoxypyridine-3-carbaldehydeHCID 4311764Sodium borohydride2×

Product 1

HCID 68512931HCID 68512931, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5-bromo-2-methoxy-pyridine-3-carbaldehyde (0.87 g, 4.03 mmol) in dry MeOH (15 mL) was treated with 4-p-tolyloxy-phenylamine (0.88 g, 4.43 mmol) and reflux for 2.5 h. The solution was cooled to 0° C. and treated slowly with NaBH4 (0.38 g, 10.1 mmol). The reaction stirred at room temperature overnight. Additional NaBH4 (0.38 g, 10.1 mmol) was added and the reaction was continued stirring for additional 6 h. The solvent was removed and the residue was partitioned between CH2Cl2 (20 mL) and water (10 mL). The organic portion was brought to the usual work-up to give a crude material. The product was yielded after chromatography purification (silica gel, 25% EtOAc/hexanes). MS (EI) 399, 401 (M+H)+.

Workup

  1. temperaturereflux for 2.5 h
  2. stirringthe reaction was continued stirring for additional 6 h
  3. customThe solvent was removed
  4. customthe residue was partitioned between CH2Cl2 (20 mL) and water (10 mL)

Sources & evidence

ORD record
ord-6a3c5efd0a644e5d901c45ad6e36b609
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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