Methanol → HCID 54685508, compound

HRID 744117Notes

Reaction equation

HRID 744117 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=O)=[C:4]([NH:12][C:13](=[O:23])[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)[CH:3]=1.C[Si](C)(C)[N-][Si](C)(C)C.[K+].C1(C)C=CC=CC=1.CO>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([C:6]([OH:8])=[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=3)[C:13](=[O:23])[NH:12]2)=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 1140TolueneHCID 3251421Potassium bis(trimethylsilyl)amideHCID 19421832HCID 19421832, compound

Product 1

HCID 54685508HCID 54685508, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the foregoing amide (0.50 g, 1.5 mmol) in tetrahydrofuran (20 ml) was added a solution of potassium hexamethyldisilazide in toluene (0.5M, 8 ml, 4 mmol) and the resulting mixture stirred for 1.5 h under a nitrogen atmosphere. Methanol (3 ml) was then added and the solution evaporated. The residue remaining was partitioned between diethyl ether (10 ml) and aqueous sodium hydroxide (0.5M, 20 ml) and the aqueous layer acidified with hydrochloric acid (5M). The precipitated solid was collected, washed with water and recrystallised from dimethylformamide to afford the title compound as a colourless solid; m.p.>320° C. (dec) (Found: C, 63.44; H, 3.89; N, 4.54. C16H12ClNO3 requires C, 63.69; H, 4.01; N, 4.64%); δH (DMSO-d6) 3.76 (3H, s, OCH3), 6.88-6.94 (3H, m, ArH), 7.20 (1H, dd, J 8.7 and 2.1 Hz, 6-H), 7.28-7.32 (2H, m, ArH), 7.91 (1H, d, J 8.7 Hz, 5-H), 10.24 (1H, br s, OH) and 11.48 (1H, s, NH); m/z 301 (M+).

Workup

  1. customthe solution evaporated
  2. customThe residue remaining was partitioned between diethyl ether (10 ml) and aqueous sodium hydroxide (0.5M, 20 ml)
  3. customThe precipitated solid was collected
  4. washwashed with water
  5. customrecrystallised from dimethylformamide

Sources & evidence

ORD record
ord-03831c88b8274ad2bba953556cf9f359
Source dataset
uspto-grants-1996_09
Patent number
US05559125

Reaction notes

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