Hydrochloric Acid → HCID 22310990, compound

HRID 967112Notes

Reaction equation

HRID 967112 reaction equation
C[O-].[Na+].C([O:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[CH:10]=[C:11]([C:26]([O:28][CH3:29])=[O:27])[N:12]2[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=1)(=O)C.Cl>CO>[Cl:25][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][C:21]=1[Cl:24])[CH2:17][N:12]1[C:13]2[C:9](=[C:8]([OH:7])[CH:16]=[CH:15][CH:14]=2)[CH:10]=[C:11]1[C:26]([O:28][CH3:29])=[O:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 22310885HCID 22310885, compound

Product 1

HCID 22310990HCID 22310990, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (92 mg) was added to methyl 4-acetoxy-N-(3,4-dichlorobenzyl)indole-2-carboxylate in methanol (10 ml) and the reaction stirred for 4 hours. The reaction was then acidified with 2 M HCl to precipitate a white solid which was filtered and dried in vacuo (0.21 g, 77%); NMR δ (CD3SOCD3) 3.80 (s, 3H), 5.74 (s, 2H), 6.45 (d, 1H), 6.75-6.82 (m, 1H), 6.95 (d, 1H), 7.04-7.15 (m, 2H), 7.30 (m, 1H), 7.41 (s, 1H), 9.89 (s, 1H); M/z (+) 318 (MH+).

Workup

  1. customto precipitate a white solid which
  2. filtrationwas filtered
  3. customdried in vacuo (0.21 g, 77%)

Sources & evidence

ORD record
ord-95daa4d8d8914a2c99a089c610bdd55a
Source dataset
uspto-grants-2005_10
Patent number
US06953809B2

Reaction notes

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