Triethylamine → HCID 19761421, compound

HRID 373843Notes

Reaction equation

HRID 373843 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[C:3](Cl)=[O:4].[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]1[CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:24][CH3:25])[CH:21]=2)[NH:16]1.CCN(CC)CC>C(Cl)Cl>[CH3:1][C:2]([CH3:7])([CH3:6])[C:3]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]1[CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:24][CH3:25])[CH:21]=2)[NH:16]1)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 19761442HCID 19761442, compound

Product 1

HCID 19761421HCID 19761421, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trimethylacetyl chloride (2.40 ml) was added dropwise to a solution of 4.68 g 2-(2-aminophenyl)-5-methoxy-2,3-dihydro-1H-indole and 3.00 ml Et3N in 150 ml CH2Cl2 at 0° C. The resulting mixture was stirred at room temperature for two hours and then quenched with water. The organic extract was washed with 7.5% NaHCO3 and sat. NaCl solution, dried (MgSO4), and concentrated to yield 5.59 g crystalline solid. Recrystallization from MeOH/water yielded 2.38 g solid, m.p. 117°-119° C.

Workup

  1. customquenched with water
  2. extractionThe organic extract
  3. washwas washed with 7.5% NaHCO3 and sat. NaCl solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-96b8cacd0ef84c9987bcfcebf49658eb
Source dataset
uspto-grants-1992_11
Patent number
US05166170

Reaction notes

Loading…