HCID 69202506, compound → HCID 69205166, compound

HRID 2378324Notes

Reaction equation

HRID 2378324 reaction equation
[CH3:1][N:2](C)[C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH2:20][CH3:21])[CH:12]=2)[OH:10])=[CH:5][CH:4]=1>C(Cl)Cl.O=[Mn]=O>[CH2:20]([O:19][C:13]1[CH:12]=[C:11]([C:9]([C:6]2[CH:5]=[CH:4][C:3]([NH:2][CH3:1])=[CH:8][CH:7]=2)=[O:10])[CH:16]=[CH:15][C:14]=1[O:17][CH3:18])[CH3:21]

Participants

4

Reactant 1

HCID 69202506HCID 69202506, compound

Product 1

HCID 69205166HCID 69205166, compoundYield 24.5%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (4-dimethylamino-phenyl)-(3-ethoxy-4-methoxy-phenyl)-methanol (1.29 g, 4.3 mmol) in CH2Cl2 (30 mL) at room temperature was added activated MnO2 powder (2.1 g, 24 mmol) and kept adding 23 equivalents of MnO2 every 3˜5 h until HPLC showed disappearance of the starting material. The black suspension was filtered through a Celite pad, concentrated in vacuo to give (3-ethoxy-4-methoxy-phenyl)-(4-methylamino-phenyl)-methanone as an brown solid (0.30 g, 23% yield): 1H NMR (CDCl3) δ 1.48 (t, J=7 Hz, 3H, CH2CH3), 2.92 (d, J=3 Hz, 3H, NCH3), 3.95 (s, 3H, OCH3), 4.16 (q, J=7 Hz, 2H, CH2CH3), 4.27 (brs, 1H, NH), 6.57-6.62 (m, 2H, Ar), 6.88-6.91 (m, 1H, Ar), 7.33-7.39 (m, 2H, Ar), 7.72-7.76 (m, 2H, Ar). The product was used in the next step without further purification.

Workup

  1. filtrationThe black suspension was filtered through a Celite pad
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4a40b428145d470c9546308f1b785eb4
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

Loading…