Sulfuric Acid → HCID 22882818, compound

HRID 863540Notes

Reaction equation

HRID 863540 reaction equation
C1([O:11][C:12]([C@H:14]2[CH2:26][CH2:25][N:17]3[C:18]4[C:23]([CH:24]=[C:16]3[CH2:15]2)=[CH:22][CH:21]=[CH:20][CH:19]=4)=[O:13])(C)CCC(C(C)C)CC1.S(=O)(=O)(O)O>>[CH:22]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:23]=1[CH:24]=[C:16]1[CH2:15][C@@H:14]([C:12]([OH:13])=[O:11])[CH2:26][CH2:25][N:17]12

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 67589174HCID 67589174, compound

Product 1

HCID 22882818HCID 22882818, compoundYield 98.6%

Procedure

To 40 g (114 mmol) of 6,7,8,9-tetrahydropyrido[1,2-a]indole-8(S)-carboxylic acid l-menthyl ester were added 50 ml of concentrated sulfuric acid and the mixture obtained was stirred until all starting material had dissolved (about 20 minutes). The solution was poured carefully into 1500 ml of ice-water and the resulting precipitate was filtered off, washed with petroleum ether/toluene (3:1) and dried to give 24.2 g of 6,7,8,9-tetrahydropyrido[1,2-a]indole-8(S)-carboxylic acid as a white solid of melting point 251°-253° C.

Workup

  1. customthe mixture obtained
  2. dissolutionhad dissolved (about 20 minutes)
  3. filtrationthe resulting precipitate was filtered off
  4. washwashed with petroleum ether/toluene (3:1)
  5. customdried

Sources & evidence

ORD record
ord-4df308d5660a49ffb97a5706514ba8b7
Source dataset
uspto-grants-1998_02
Patent number
US05721230

Reaction notes

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