Water → HCID 67254243, compound

HRID 2042063Notes

Reaction equation

HRID 2042063 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:8][C:9]2[CH:10]=[C:11]([CH:14]=[C:15]([N+:17]([O-])=O)[CH:16]=2)[C:12]#[N:13])[CH:5]=[N:6][CH:7]=1.O.C([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C.[Fe]>[NH2:17][C:15]1[CH:14]=[C:11]([CH:10]=[C:9]([O:8][C:4]2[CH:5]=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[CH:16]=1)[C:12]#[N:13]

Participants

6

Reactant 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 67253527HCID 67253527, compound

Product 1

HCID 67254243HCID 67254243, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

Iron powder (6.3 g, 112 mmol) was added to a mixture of 3-(5-chloro-pyridin-3-yloxy)-5-nitro-benzonitrile (3.1 g, 11.2 mol) in acetic acid (100 mL) and the reaction was stirred at RT for 6 h. Water (200 mL) was added and the mixture was neutralized to pH 7 with saturated Na2CO3 solution and was extracted with EtOAc (3×150 mL). The combined organics were washed with brine, dried (Na2SO4), concentrated in vacuo and purified on silica gel to give 3-amino-5-(5-chloropyridin-3-yloxy)benzonitrile (1.92 g, 71% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.53 (d, J=1.6 Hz, 1H), 8.44 (d, J=2.4 Hz, 1H), 7.80 (t, J=2.4 Hz, 1H), 6.77 (s, 1H), 6.72 (d, J=1.6 Hz, 1H), 6.56 (d, J=2.0 Hz, 1H), 5.92 (s, 2H); MS (ESI) m/z: 246.2 [M+H]+.

Workup

  1. extractionwas extracted with EtOAc (3×150 mL)
  2. washThe combined organics were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. custompurified on silica gel

Sources & evidence

ORD record
ord-7012e63944784ad38881d79d4d32fe11
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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