Thionyl Chloride → HCID 5311907, compound

HRID 657702Notes

Reaction equation

HRID 657702 reaction equation
S(Cl)(Cl)=O.[CH2:5]1C2NC3C(=CC=C(C(O)=O)C=3)C=2CCC1.[CH2:21]1[C:33]2[NH:32][C:31]3[CH:30]=[CH:29][CH:28]=[C:27]([C:34]([OH:36])=[O:35])[C:26]=3[C:25]=2[CH2:24][CH2:23][CH2:22]1>CO>[CH2:21]1[C:33]2[NH:32][C:31]3[CH:30]=[CH:29][CH:28]=[C:27]([C:34]([O:36][CH3:5])=[O:35])[C:26]=3[C:25]=2[CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 6461364HCID 6461364, compoundHCID 64639662,3,4,9-tetrahydro-1H-carbazole-5-carboxylic acid

Product 1

HCID 5311907HCID 5311907, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

By adding thionyl chloride to a methanol solution of a mixture of 2,3,4,9-tetrahydro-1H-carbazole-7-carboxylic acid and 2,3,4,9-tetrahydro-1H-carbazole-5-carboxylic acid at −10° C., followed by the reaction under heating and subsequent separation and purification by a column chromatography, methyl 2,3,4,9-tetrahydro-1H-carbazole-7-carboxylate [Reference Example 17a: ESI: 2230 (M+H)+] and methyl 2,3,4,9-tetrahydro-1H-carbazole-5-carboxylate [Reference Example 17b: ESI: 230 (M+H)+] were obtained.

Workup

  1. customfollowed by the reaction
  2. temperatureunder heating
  3. customsubsequent separation and purification by a column chromatography, methyl 2,3,4,9-tetrahydro-1H-carbazole-7-carboxylate [Reference Example 17a: ESI: 2230 (M+H)+]

Sources & evidence

ORD record
ord-4b078ee7227c4465a42bcce0632a569b
Source dataset
uspto-grants-2011_12
Patent number
US08076348B2

Reaction notes

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