Triethylamine → HCID 178480112, compound

HRID 1297509Notes

Reaction equation

HRID 1297509 reaction equation
C([O:5][C:6]1[C:7](=[O:24])[C:8](=O)[C:9]=1[CH:10]=[C:11]1[C:19]([CH3:21])([CH3:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]1[CH3:22])CCC.Cl.[NH2:26][OH:27].C(N(CC)CC)C>C(O)C>[OH:5][C:6]1[C:7](=[O:24])[C:8](=[N:26][OH:27])[C:9]=1[CH:10]=[C:11]1[C:19]([CH3:21])([CH3:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]1[CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 58915119HCID 58915119, compound

Product 1

HCID 178480112HCID 178480112, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 200 mg (0.61 mmol)of 3-butoxy-4-(1,3,3-trimethyl-2,3-dihydro-1H-2-indolylidenmethyl)-3-cyclobutene-1,2-dione (18), 50 mg (0.72 mmol) of hydroxylamine hydrochloride and 90 μl (0.64 mmol) of triethylamine is stirring in 8 ml of absolute ethanol at room temperature for 1 h and 30 min at 40° C. The solvent is removed under reduced pressure by a rotary evaporator. The obtained residue is column purified (Silica gel 60, 0–10% methanol-chloroform) to give 2-hydroxy-4-hydroxyimino-3-(1,3,3-trimethyl-2,3-dihydro-1H-2-indolylidenmethyl)-2-cyclobuten-1-one (19a) as an yellow solid. Yield: 80 mg (46%).

Workup

  1. customThe solvent is removed under reduced pressure by a rotary evaporator
  2. custompurified (Silica gel 60, 0–10% methanol-chloroform)

Sources & evidence

ORD record
ord-570e3b7598d749bdba86687f49f84815
Source dataset
uspto-grants-2007_07
Patent number
US07250517B2

Reaction notes

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