Einecs 211-027-4 → 2-Anilinophenol

HRID 403141Notes

Reaction equation

HRID 403141 reaction equation
[Cl-].[NH+]1C=CC=CC=1.C[O:9][C:10]1[CH:22]=[CH:21][CH:20]=[CH:19][C:11]=1[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>Cl>[C:13]1([NH:12][C:11]2[CH:19]=[CH:20][CH:21]=[CH:22][C:10]=2[OH:9])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 69401Einecs 211-027-4HCID 109105142-methoxyphenylaniline

Product 1

HCID 1861332-Anilinophenol

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
200 °C

Procedure

A 1 L three neck flask was charged with pyridinium chloride (52.2 g, 452 mmol) and 2-methoxy-N-phenylaniline (9 g, 45.2 mmol). The reaction mixture was heated to 200° C. for 4 hours. The reaction mixture was poured into 5% HCl (200 mL) and extracted with EtOAc (3×300 mL). The organic portion was combined and purified by column chromatography (100% DCM) to yield the desired product. (6.5 g, 77%)

Workup

  1. extractionextracted with EtOAc (3×300 mL)
  2. custompurified by column chromatography (100% DCM)

Sources & evidence

ORD record
ord-c3c03e6426b941b9b975b0a8f9bdff44
Source dataset
uspto-grants-2014_06
Patent number
US08748011B2

Reaction notes

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