Hydrochloric Acid → HCID 19935699, compound

HRID 484261Notes

Reaction equation

HRID 484261 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH:9]=[C:8]([CH:15]([CH3:19])[C:16]([OH:18])=[O:17])[CH:7]=[CH:6][C:5]2=1.[OH-].[Na+].Cl[CH2:23][C:24]1[CH:33]=[CH:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:25]=1.Cl>O.CS(C)=O>[CH3:19][CH:15]([C:8]1[CH:7]=[CH:6][C:5]2[C:4]3[C:12](=[CH:13][CH:14]=[C:2]([O:1][CH2:23][C:24]4[CH:33]=[CH:32][C:31]5[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=5)[N:25]=4)[CH:3]=3)[N:11]([CH2:23][C:24]3[CH:33]=[CH:32][C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]=3)[C:10]=2[CH:9]=1)[C:16]([OH:18])=[O:17]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 203942-(Chloromethyl)quinolineHCID 199357086-Hydroxy-a-methyl carbazole-2-acetic acid

Product 1

HCID 19935699HCID 19935699, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture consisting of 6-hydroxy-α-methyl carbazole-2-acetic acid (2.6 g, 0.010 mol), dimethyl sulfoxide (200 mL), sodium hydroxide (2.0 g in 20 mL H2O, 0.05 mol) and 2-chloromethylquinoline.HCl (4.0 g, 0.018 mol) is heated to 80° C. for 3 hours. The reaction mixture is cooled, poured into water (1000 mL), and the pH is adjusted to 4 with 1N HCl. The aqueous solution is extracted with ethyl acetate (4×300 mL) and the organic layers are combined, washed with water (2×300 mL), once with brine (300 mL), dried over MgSO4, filtered and concentrated to give 3.0 g of crude product. The latter is chromatographed on silica gel using 10% methanol/methylene chloride as an eluent to give 8 g of product, m.p. 197°-199° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. extractionThe aqueous solution is extracted with ethyl acetate (4×300 mL)
  3. washwashed with water (2×300 mL), once with brine (300 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give 3.0 g of crude product
  8. customThe latter is chromatographed on silica gel using 10% methanol/methylene chloride as an eluent

Sources & evidence

ORD record
ord-52eeed196e254b1b83f8c86a5928f6bc
Source dataset
uspto-grants-1993_07
Patent number
US05229516

Reaction notes

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