Methanol → HCID 15337216, compound

HRID 1439905Notes

Reaction equation

HRID 1439905 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH2:14][C:6]3=[C:7]([C:11]([OH:13])=[O:12])[NH:8][C:9]([CH:10]=1)=[C:5]23.S(Cl)(Cl)=O.[CH3:21]O>>[Cl:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH2:14][C:6]3=[C:7]([C:11]([O:13][CH3:21])=[O:12])[NH:8][C:9]([CH:10]=1)=[C:5]23

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl Chloride2×HCID 15337215HCID 15337215, compound

Product 1

HCID 15337216HCID 15337216, compoundYield 37%

Procedure

To a solution of 7-chloro-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylic acid (8 g) in MeOH (100 mL) was added thionyl chloride (6.2 mL) at 0° C. The mixture was refluxed for 13 h, while thionyl chloride (10 mL×4) was added during the reflux. The resulting mixture was concentrated and the residue was purified by silica gel column chromatography with 15:1~1:1 hexane/ethyl acetate to give 2.47 g of the title compound (37%): 1H NMR (CDCl3) δ8.52 (bs, 1H), 7.15 (d, 1H, J=1.5 Hz), 6.84 (d, 1H, J=1.5 Hz), 3.93 (s, 3H), 3.07 (t, 2H, J=6.3 Hz), 2.90 (t, 2 H, J=6.3 Hz), 2.07 (5et, 2H, J=6.3 Hz).

Workup

  1. additionwas added during the reflux
  2. concentrationThe resulting mixture was concentrated
  3. customthe residue was purified by silica gel column chromatography with 15:1~1:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-ee447b2fbecd4758a8cded2ac52bcd9d
Source dataset
uspto-grants-1996_03
Patent number
US05496843

Reaction notes

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