Ammonium Chloride → HCID 11673048, compound

HRID 885088Notes

Reaction equation

HRID 885088 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:19])[CH:7]=[CH:8][C:9]=1/[CH:10]=[CH:11]/[C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)([O-])=O.[Cl-].[NH4+]>CC(C)=O.O.[Zn]>[NH2:1][C:4]1[CH:5]=[C:6]([OH:19])[CH:7]=[CH:8][C:9]=1/[CH:10]=[CH:11]/[C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 11579752HCID 11579752, compound

Product 1

HCID 11673048HCID 11673048, compoundYield 81.2%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalyst2×HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of the product of 3-nitro-4-[(E)-2-(4-hydroxyphenyl)-vinyl]phenol (216 mg, 0.84 mmol) in acetone (6 mL) was added a solution of ammonium chloride (89.9 mg, 1.68 mmol) in 2 mL of water. The mixture was heated to reflux, and the oil bath was removed. Zinc dust (164.8 mg, 2.5 mmol) was added in small portions to the reaction mixture to maintain a moderate reaction. After the reaction subsided an additional portion of zinc (82.4 mg, 1.25 mmol) was added. The reaction mixture was then heated to reflux for an additional 2 h. The precipitate was removed by filtration, washed with acetone (2×20 mL) and with ethyl acetate (2×30 mL). The combined washings were concentrated in vacuo and the crude product was purified by column chromatography using 5% methanol in dichloromethane to afford 3-Amino-4-[(E)-2-(4-hydroxy-phenyl)vinyl]phenol (155 mg, 72%). MS (ES) m/z: 228.11 (M+11), 134.06; 13C-NMR (DMSO-d6): δ 158.3, 156.9, 147.9, 130.4, 130.2, 127.9, 126.9, 124.5, 122.0, 115.9, 115.5, 114.2, 105.4, 102.2. Mp. 229-232° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. customthe oil bath was removed
  4. temperatureto maintain
  5. customa moderate reaction
  6. additionwas added
  7. temperatureThe reaction mixture was then heated
  8. temperatureto reflux for an additional 2 h
  9. customThe precipitate was removed by filtration
  10. washwashed with acetone (2×20 mL) and with ethyl acetate (2×30 mL)
  11. concentrationThe combined washings were concentrated in vacuo
  12. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-547a049596a640c488f8f5e55e3a7e30
Source dataset
uspto-grants-2012_08
Patent number
US08242144B2

Reaction notes

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