Acetyl chloride → (2-Amino-4-methoxyphenyl)(phenyl)methanone

HRID 983896Notes

Reaction equation

HRID 983896 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[CH:4]=1.B(Cl)(Cl)Cl.[C:14](Cl)([CH3:16])=[O:15].[Al+3].[Cl-].[Cl-].[Cl-].[OH-].[Na+]>C(Cl)Cl.CCCCCCC>[NH2:9][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[C:14]([C:16]1[CH:7]=[CH:8][CH:3]=[CH:4][CH:5]=1)=[O:15]

Participants

8

Reactant 5

HCID 6367Acetyl chlorideHCID 108243-MethoxyanilineHCID 14798Sodium HydroxideHCID 25135Boron TrichlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 254180(2-Amino-4-methoxyphenyl)(phenyl)methanone

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8900HeptaneSolvent

Procedure

Step D) To a solution of 21.8 g (172 mmol) of m-anisidine in 800 mL of CH2Cl2 cooled to −50° C., was added 172 mL (172 mmol) of 1M BCl3 in heptane over 20 min to produce an amber colored mixture which was stirred 1 h. To this mixture was added 12.2 mL (172 mmol) of AcCl and 22.9 g (172 mmol) of AlCl3. The mixture was allowed to warm to room temperature overnite, poured into ice water, the solution adjusted to pH 9 using 10% aqueous NaOH and was extracted repeatedly using EtOAC. The combined organic extracts were washed with brine, dried (MgSO4), concentrated and the resulting solid recrystallized from the minimal amount of MeOH in CH2Cl2/hexanes (50%) to afford 13.4 g (47%)of slightly impure 2-amino-4-methoxybenzophenone as a crystalline solid. The solid could be taken directly into the next reaction or purified to absolute purity over SiO2 (eluted with 0% to 14% MeOH/CH2Cl2): 1H NMR (500 MHz, CDCl3) δ 2.50 (s, 3H), 3.79 (s, 3H), 6.05 (d, J=2.4 Hz, 1H), 6.21 (dd, J=8.8, 2.4 Hz, 1H), 6.38 (m, 2H), 7.62 (d, J=8.8 Hz, 1H)

Workup

  1. customto produce an amber colored mixture which
  2. extractionwas extracted repeatedly using EtOAC
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customthe resulting solid recrystallized from the minimal amount of MeOH in CH2Cl2/hexanes (50%)

Sources & evidence

ORD record
ord-979a22c31a9141cc9e94f9de7e321263
Source dataset
uspto-grants-2005_03
Patent number
US06867185B2

Reaction notes

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