1,2-Dichloroethane → 2-[3-(Amino)benzoyl]-9-methyl-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]-indole

HRID 1368114Notes

Reaction equation

HRID 1368114 reaction equation
Cl.[CH3:2][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]2[CH2:12][CH2:13][NH:14][CH2:15][C:4]1=2.[NH2:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=1)[C:20](O)=[O:21].O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.C(Cl)CCl>CN(C=O)C.O>[NH2:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=1)[C:20]([N:14]1[CH2:13][CH2:12][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[N:3]([CH3:2])[C:4]=2[CH2:15]1)=[O:21]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 74193-Aminobenzoic AcidHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 224011859-methyl-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]-indole mono hydrochloride

Product 1

HCID 98613092-[3-(Amino)benzoyl]-9-methyl-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]-indoleYield 92.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 9-methyl-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]-indole mono hydrochloride (0.35 g, 1.59 mmole) in dry DMF (20 mL) at RT was added 3-aminobenzoic acid (0.24 g, 1.75 mmole), 1-hydroxybenzotriazole hydrate (0.24 g, 1.75 mmole) and diisopropylethylamine (0.45 g, 3.50 mmole). After 10 min, EDC (0.33 g, 1.75 mmole) was added and the reaction was allowed to stir for 12 hr. The reaction contents were poured into H2O (100 mL) and extracted with EtOAc (2×100 mL). The combined organic phases were washed sequentially with H2O and brine, then were dried over Na2SO4. Concentration under reduced pressure gave a yellow oil. Purification on silica (CHC13/CH3OH, 95:5) afforded the title compound (0.45 g, 92%) as a white solid: MS (ES) m/e 306 (M+H)+.

Workup

  1. customThe reaction contents
  2. extractionextracted with EtOAc (2×100 mL)
  3. washThe combined organic phases were washed sequentially with H2O and brine
  4. dry with materialwere dried over Na2SO4
  5. concentrationConcentration under reduced pressure
  6. customgave a yellow oil
  7. customPurification on silica (CHC13/CH3OH, 95:5)

Sources & evidence

ORD record
ord-84237c49a275449aa554c7bd19f0dcda
Source dataset
uspto-grants-2003_06
Patent number
US06573272B1

Reaction notes

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