HCID 66750571, compound → HCID 66750722, compound

HRID 643900Notes

Reaction equation

HRID 643900 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([Br:22])=[C:11]2[C:16](=[CH:17][C:18]=1[N+:19]([O-])=O)[CH2:15][CH2:14][CH2:13][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CC(O)=O.CCO.[Fe]>[CH2:1]([O:8][C:9]1[C:18]([NH2:19])=[CH:17][C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[C:10]=1[Br:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 66750571HCID 66750571, compound

Product 1

HCID 66750722HCID 66750722, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 18476134Acetic acid ethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 6-benzyloxy-5-bromo-7-nitro-1,2,3,4-tetrahydronaphthalene (0.50 g, 1.38 mmol) in AcOH/EtOH (3:1, 20 mL), is added iron powder (0.50 g, 9.25 mmol). The mixture is heated at 100° C. for 2 h. The precipitate is filtered through Celite. The filtrate is concentrated, extracted with water and CH2Cl2, and filtered. The crude material is purified via Biotage, eluting with 0-20% EtOAc/hexanes, to afford 3-benzyloxy-4-bromo-5,6,7,8-tetrahydronaphthalen-2-ylamine: (M+H)=333, 334.

Workup

  1. filtrationThe precipitate is filtered through Celite
  2. concentrationThe filtrate is concentrated
  3. extractionextracted with water and CH2Cl2
  4. filtrationfiltered
  5. customThe crude material is purified via Biotage
  6. washeluting with 0-20% EtOAc/hexanes

Sources & evidence

ORD record
ord-a1ce7d5c1b704bc2b29d07784f31dd4c
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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