Sulfuric Acid → HCID 22247299, compound

HRID 1531993Notes

Reaction equation

HRID 1531993 reaction equation
N1C2C(=CC=CC=2)C[CH2:2]1.[CH2:10]([N:18]1[C:26]2[C:21](=[CH:22][C:23]([C:31]([OH:33])=[O:32])=[C:24]([CH3:30])[C:25]=2[N+:27]([O-:29])=[O:28])[CH2:20][CH2:19]1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].S(=O)(=O)(O)O>CO>[CH2:10]([N:18]1[C:26]2[C:21](=[CH:22][C:23]([C:31]([O:33][CH3:2])=[O:32])=[C:24]([CH3:30])[C:25]=2[N+:27]([O-:29])=[O:28])[CH2:20][CH2:19]1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10328Indoline2×HCID 22247310HCID 22247310, compound

Product 1

HCID 22247299HCID 22247299, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.88 (3H, br-t, J=7 Hz, —(CH2)7CH3), 1.00˜1.70 (121H, m, —H2(CH2)f—), 2.47 (3H, s, indoline C6—CH3), 3.02 (2H, t, J=8 Hz, indoline C3—H2), 3.03 (2H, t, J=7 Hz, >NCH2—), 3.69 (2H, t, J=8 Hz, indoline C2—H2), 5.00 (IH, br, -2H), 7.73 (1H, s, indoline C4—H). (4) 1-Octyl-5-carboxy-6-methyl-7-nitroindoline (1.4 g) was dissolved in methanol (30 ml), and conc. sulfuric acid (4.1 g) was added, which was followed by refluxing for 4 hr. Methanol was evaporated under reduced pressure. Ethyl acetate (100 ml) was added to the residue. The mixture was washed with water and dried over anhydrous sodium sulfate. Ethyl acetate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform/ methanol=1/10−10/1) to give 750 mg of 1-octyl-5-methoxycarbonyl-6-methyl-7-nitroindoline as crystals.

Workup

  1. temperatureby refluxing for 4 hr
  2. customMethanol was evaporated under reduced pressure
  3. additionEthyl acetate (100 ml) was added to the residue
  4. washThe mixture was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customEthyl acetate was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: chloroform/ methanol=1/10−10/1)

Sources & evidence

ORD record
ord-4c49839221934920b01085059023bbd2
Source dataset
uspto-grants-2001_03
Patent number
US06200988B1

Reaction notes

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