2,5-Dimethylaniline → N-[5-(Hydroxymethyl)-2-methylphenyl]acetamide

HRID 1263436Notes

Reaction equation

HRID 1263436 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([C:7]([CH3:10])=[CH:8][CH:9]=1)[NH2:6].CC1C=CC(C)=CC=1N.[C:20](OC(=O)C)(=[O:22])[CH3:21].C([O-])(=O)C.[K+]>C(Cl)(Cl)Cl>[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([C:7]([CH3:10])=[CH:8][CH:9]=1)[NH:6][C:20]([CH3:21])=[O:22]

Participants

6

Reactant 4

HCID 72592,5-DimethylanilineHCID 7918Acetic AnhydrideHCID 517044Potassium AcetateHCID 586243(3-Amino-4-methylphenyl)methanol

Product 1

HCID 14543056N-[5-(Hydroxymethyl)-2-methylphenyl]acetamideYield 114.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of an approximately 1:1 mixture of 3-(hydroxymethyl)-6-methylaniline, (8.05 g, 58.8 mmol) (96) and 2,5-dimethylaniline in chloroform (290 mL), was added acetic anhydride (20 mL, 206 mmol) and potassium acetate (20 g, 202 mmol). The resulting mixture was heated to its reflux temperature for 2 hours. The mixture was then concentrated and purified by a flash column chromatography (1:1 of hexane-ethyl acetate) which also removed the by-product from Example 74 to give the title compound (12.02 g, 92%). TLC Rf: 0.52 (ethyl acetate); MS (electrospray) 222 (M+1); 1H N MR (CDCl3) δ2.09 (s, 3H), 2.21 (s, 3H), 2.25 (s, 3H), 5.06 (s, 2H), 7.00 (br s, 1H, NH), 7.08 (d, 1H, J=7.6 Hz), 7.18 (d, 1H, J=7.6 Hz), 7.81 (s, 1H).

Workup

  1. temperatureThe resulting mixture was heated to its
  2. temperaturereflux temperature for 2 hours
  3. concentrationThe mixture was then concentrated
  4. custompurified by a flash column chromatography (1:1 of hexane-ethyl acetate) which
  5. customalso removed the by-product from Example 74

Sources & evidence

ORD record
ord-3e59d082c8584dc6857a2600abafadcb
Source dataset
uspto-grants-2003_04
Patent number
US06541467B1

Reaction notes

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