HCID 66699830, compound → HCID 24985363, compound

HRID 388103Notes

Reaction equation

HRID 388103 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:17]2[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=2)=[N:6][C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16].[CH3:24][O:25]C1C=CC=CC=1NC1N=C(C2C=C(O)C=CC=2)C=CC=1[N+]([O-])=O>C(O)(=O)C.[Fe]>[OH:23][C:19]1[CH:18]=[C:17]([C:5]2[N:6]=[C:7]3[N:8]([C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[O:15][CH3:16])[C:24](=[O:25])[NH:1][C:2]3=[CH:3][CH:4]=2)[CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 66699830HCID 66699830, compoundHCID 66699831HCID 66699831, compound

Product 1

HCID 24985363HCID 24985363, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

3-(5-Amino-6-(2-methoxyphenylamino)pyridin-2-yl)phenol. 3-(6-(2-Methoxyphenyl-amino)-5-nitropyridin-2-yl)phenol (1.48 g, 4.39 mmol) was dissolved in glacial acetic acid (120 mL). Iron powder (0.489 g, 8.78 mmol) was then added and the solution heated to 80° C. The reaction was monitored via thin layer chromatography for starting material consumption. After 2 h, the solution was cooled and filtered through celite and condensed under reduced pressure. The resultant oil was partitioned between sodium bicarbonate solution and ethyl acetate (3×). The organics were combined, dried over magnesium sulfate, filtered and solvent removed under reduced pressure to afford the title compound (1.15 g, 85%). MS (ESI) m/z 308.4 [M+1]+.

Workup

  1. custommaterial consumption
  2. temperaturethe solution was cooled
  3. filtrationfiltered through celite and condensed under reduced pressure
  4. customThe resultant oil was partitioned between sodium bicarbonate solution and ethyl acetate (3×)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customsolvent removed under reduced pressure

Sources & evidence

ORD record
ord-60d834a9a60b499ea0a3c13dcc632d54
Source dataset
uspto-grants-2013_02
Patent number
US08372976B2

Reaction notes

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