Hydrochloric Acid → HCID 10888757, compound

HRID 1884402Notes

Reaction equation

HRID 1884402 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=O)C.Cl>CO.O>[NH:4]1[C:12]2[C:7](=[CH:8][C:9]([CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 11299248HCID 11299248, compound

Product 1

HCID 10888757HCID 10888757, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 2 (1.75 g, 7.5 mmol) in a mixture of methanol (100 mL), water (20 mL) and conc. HCl (10 mL) was refluxed for 4 h. The solution was diluted with water (30 mL), concentrated to about 50 mL, basified to pH 8 with K2CO3 and extracted with EtOAc. The combined organic phases were washed with brine, dried and evaporated to give methyl indoline-5-acetate 3 as a brown oil (1.06 g, 74%); 1H NMR: δH (90 MHz) 6.80-7.06 (m, 2H), 6.58 (d, J=8 Hz, 1H), 3.64 (s, 3H), 3.52 (t, J=7.2 Hz, 3H), 3.50 (s, 2H) and 2.96 (t, J=7.2 Hz, 2H). The crude product and glutaric anhydride (685 mg, 6 mmol) were dissolved in chloroform (75 mL) and the mixture was stirred at rt overnight, then refluxed for 2 h. The solution was extracted with saturated aq. NaHCO3 solution and the aqueous extract was acidified to pH 2.8 with conc. HCl and extracted with EtOAc. The latter organic extracts were dried and evaporated to give 4 as white crystals (1.24 g, 74%), mp 134-136° C. (EtOAc-hexanes); IR: νmax/cm−1; 1720, 1.625, 1605; 1H NMR: δH (400 MHz) 8.15 (d, J=8 Hz, 1H), 7.07-7.11 (m, 2H), 4.04 (t, J=8.5 Hz, 2H), 3.68 (s, 3H), 3.57 (s, 2H), 3.18 (t, J=8.5 Hz, 2H), 2.52 (t, J=7 Hz, 4H), and 2.06 (quintet, J=7 Hz, 2H). Anal. Calcd for C16H19NO5: C, 56.11; H, 5.07; N,. 10.06. Found: C, 56.18; H, 4.86; N, 10.03.

Workup

  1. temperaturewas refluxed for 4 h
  2. concentrationconcentrated to about 50 mL
  3. extractionextracted with EtOAc
  4. washThe combined organic phases were washed with brine
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-ac0e38b8ae7e43969ab4b490ca2f18ea
Source dataset
uspto-grants-2004_07
Patent number
US06765014B1

Reaction notes

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