2-(3-Bromo-propoxy)-5-nitro-biphenyl → 6-(3-Bromo-propoxy)-biphenyl-3-ylamine

HRID 271099Notes

Reaction equation

HRID 271099 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][C:7]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C.Cl>[Br:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:8][C:9]([NH2:12])=[CH:10][CH:11]=1

Participants

4

Reactant 1

HCID 223531762-(3-Bromo-propoxy)-5-nitro-biphenyl

Product 1

HCID 223532056-(3-Bromo-propoxy)-biphenyl-3-ylamineYield 52%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

2-(3-Bromo-propoxy)-5-nitro-biphenyl (q, 530 mg, 1.57 mmol) was refluxed with stannous chloride hydrate (1.1 g, 4.8 mmol) in 5 mL ethanol and 3 mL concentrated HCl. After 1.5 hours, the solvent was evaporated and the mixture was basified with 2N NaOH. The mixture was then extracted with DCM, dried and evaporated, affording 250 mg 6-(3-bromo-propoxy)-biphenyl-3-ylamine (r) in 50% yield: 1H NMR (500 MHz, CDCl3): 7.3 (m, 5H), 6.7 (m, 3H), 4.2 (bs, 2H), 3.9 (m, 2H), 3.5 (m, 2H) and 2.1 (2H).

Workup

  1. customthe solvent was evaporated
  2. extractionThe mixture was then extracted with DCM
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-207420f763434cd59d5736f843edaae5
Source dataset
uspto-grants-2008_11
Patent number
US07452873B2

Reaction notes

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