Hydrochloric Acid → Phenol, 3-(methylamino)-4-nitro-

HRID 1890918Notes

Reaction equation

HRID 1890918 reaction equation
F[C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].Cl.[CH3:13][NH2:14]>>[CH3:13][NH:14][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 146175Phenol, 3-(methylamino)-4-nitro-Yield 98%

Conditions

Temperature
85 °C

Procedure

To a pressure vessel was added 3-fluoro-4-nitro-phenol (5.0 g, 31.82 mmol) and a 40% aqueous solution of methylamine (10 mL). The reaction mixture was stirred at 85° C. for 5 h, then it was cooled to room temperature, poured on water, and acidified to pH 1 with 1 N aqueous HCl. The resulting precipitate was filtered, washed with water, and dried in vacuo to give 5.23 g of 3-methylamino-4-nitro-phenol as an orange solid (98% yield): 1H NMR (DMSO-d6) δ 2.88 (d, 3H), 6.14 (dd, 1H), 6.17 (d, 1H), 7.96 (d, 1H), 8.25 (q, 1H), 10.8 (broad s, 1H); MS (m/z) 167 [M−H]−.

Workup

  1. temperatureit was cooled to room temperature
  2. additionpoured on water
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-f1ac862ebeeb4c53a7d5132e2782daca
Source dataset
uspto-grants-2013_08
Patent number
US08507489B2

Reaction notes

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