Hydrochloric Acid → 7-Methylisatin

HRID 1413964Notes

Reaction equation

HRID 1413964 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=C2[C:10]=1[NH:9]C(=S)C2C.[CH3:13][C:14](C)([O-:16])[CH3:15].[K+].Cl.[O:20]1CCCC1>O.[Cl-].[Na+].O>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:13]2[C:10]=1[NH:9][C:15](=[O:20])[C:14]2=[O:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 20289272HCID 20289272, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 143137-MethylisatinYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Utilizing the general procedure, 3.30 g of 7-methyl-3-methylthiooxindole and an E.Q. of sublimed potassium t-butoxide in 250 ml of tetrahydrofuran was stirred and vigorously aerated for 6 h at 0° C. and 18 h at 25° C. Acidification with 1.42 ml of conc. hydrochloric acid in 20 ml of water, followed by addition of a saturated brine solution, gave an organic layer which was separated and worked up as described above to give 1.98 g of crude product. Recrystallization from methanol gave 1.09 g (40% yield) of 7-methylisatin, mp 268°-270° C.

Workup

  1. customgave an organic layer which
  2. customwas separated
  3. customto give 1.98 g of crude product
  4. customRecrystallization from methanol

Sources & evidence

ORD record
ord-9a37b9b7585b4d8281f26ace049d125c
Source dataset
uspto-grants-1981_02
Patent number
US04252723

Reaction notes

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