O-Xylene → HCID 10708148, compound

HRID 366816Notes

Reaction equation

HRID 366816 reaction equation
[N:1]([C:4](=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][Cl:18])=[C:11]([O:19][CH3:20])[CH:10]=1)[C:5]([O-:7])=[O:6])=[N+]=[N-].[C:21]1(C)C(C)=CC=CC=1>>[Cl:18][CH2:17][CH2:16][O:15][C:12]1[CH:13]=[C:14]2[C:9]([CH:8]=[C:4]([C:5]([O:7][CH3:21])=[O:6])[NH:1]2)=[CH:10][C:11]=1[O:19][CH3:20]

Participants

3

Reactant 2

HCID 7237O-XyleneHCID 131722121HCID 131722121, compound

Product 1

HCID 10708148HCID 10708148, compoundYield 52%

Procedure

A warmed (40° C.) solution of the above azidocinnamate (5.08 g, 16.3 mmol) in xylenes (140 mL) was added to boiling xylenes (60 mL) over 1 h. After a further 15 min at reflux, most of the xylene was removed by distillation. The precipitate that formed in the cooled residue was isolated by filtration, washed with CHCl3 and hexanes, and crystallized from MeOH to give methyl 6-(2-chloroethoxy)-5-methoxyindole-2-carboxylate (2.423 g, 52%) as fluffy white needles, mp 164-166° C. (sublimes 110° C.). 1H NMR [(CD3)2SO] δ 11.65 (br s, 1 H, NH), 7.13 (s, 1 H, H-4), 7.03 (d, J=1.6 Hz, 1 H, H-3), 6.91 (s, 1 H, H-7), 4.24 (t, J=5.2 H, 2 H, OCH2), 3.98 (t, J=5.2 H, 2 H, CH2Cl), 3.84 3.78 (2×s, 3 H each, OCH3); 13C NMR δ 161.5 (CO2), 147.8, 145.8, 132.4, 125.5, 120.3 (C-2, 3a, 5, 6, 7a), 107.8 (C-3), 103.0 (C-4), 96.3 (C-7), 68.9 (OCH2), 55.7 (OCH3), 51.4 (CO2CH3), 42.9 (CH2Cl).

Workup

  1. additionwas added
  2. customover 1 h
  3. customwas removed by distillation
  4. customThe precipitate that formed in the cooled residue
  5. customwas isolated by filtration
  6. washwashed with CHCl3 and hexanes
  7. customcrystallized from MeOH

Sources & evidence

ORD record
ord-3d6ebfc4a4574b069849b39ea5d99c1b
Source dataset
uspto-grants-2000_10
Patent number
US06130237

Reaction notes

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