Toluene → HCID 54738210, compound

HRID 744126Notes

Reaction equation

HRID 744126 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].C1(C)C=CC=CC=1.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[O:24][C:25]1[CH:26]=[C:27]([CH2:31][C:32]([O:34]C)=O)[CH:28]=[CH:29][CH:30]=1.[NH2:36][C:37]1[CH:46]=[C:45]([Cl:47])[CH:44]=[CH:43][C:38]=1[C:39](OC)=[O:40]>C1COCC1.CO>[Cl:47][C:45]1[CH:46]=[C:37]2[C:38]([C:39]([OH:40])=[C:31]([C:27]3[CH:28]=[CH:29][CH:30]=[C:25]([O:24][C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=4)[CH:26]=3)[C:32](=[O:34])[NH:36]2)=[CH:43][CH:44]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 80001Methyl 4-chloroanthranilateHCID 3251421Potassium bis(trimethylsilyl)amideHCID 54273101HCID 54273101, compound

Product 1

HCID 54738210HCID 54738210, compoundYield 59.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Potassium bis(trimethylsilyl)amide in toluene (0.5M, 10.8 ml, 5.4mmol) was added dropwise to a solution of methyl [3-(2-pyridyloxy)phenyl]acetate (0.52 g, 2.14 mmol) and methyl 2-amino-4-chlorobenzoate (0.43 g, 2.32 mmol) in dry THF (30 ml). The reaction mixture was stirred at room temperature for 3 1hours then methanol (10 ml) was added. The solution was concentrated in vacuo, the residue was dissolved in 0.5M sodium hydroxide (25 ml) and washed with diethyl ether (2×25 ml). The aqueous phase was acidified with 5M hydrochloric acid. The resultant precipitate was collected and recrystallised from dimethylformamide/water to afford the title compound as a pale cream solid (0.463 g, 59%). A further recrystallisation from propan-2-ol gave analytically pure material; m.p. 269°-271° C. (from propan-2-ol) (Found: C, 65.92;H, 3.71;N, 7.59. C20H13ClN2O3 requires C, 65.85;H, 3.71;N, 7.68%); δH (360 MHz, DMSO-d6) 7.03-7.14 (4H, m, ArH), 7.23 (1H, dt, J 2, 8.5 Hz, ArH), 7.32 (1H, d, J 2 Hz, ArH), 7.43 (1H, t, J 8 Hz, 5'-H), 7.85 (1H, m, ArH), 7.94 (1H, d, J 8.7 Hz, 5-H), 8.18 (1H, dd, J 5, 2 Hz, 6"-H), 10.46 (1H, br s, OH), 11.55 (1H, br s, NH); m/z 364 (M+).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutionthe residue was dissolved in 0.5M sodium hydroxide (25 ml)
  3. washwashed with diethyl ether (2×25 ml)
  4. customThe resultant precipitate was collected
  5. customrecrystallised from dimethylformamide/water

Sources & evidence

ORD record
ord-a70927748cbd420abdb9ea88306d0d8f
Source dataset
uspto-grants-1996_09
Patent number
US05559125

Reaction notes

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