Aniline → HCID 11173500, compound

HRID 1796693Notes

Reaction equation

HRID 1796693 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=O)[CH2:6][C@@H:5]1[CH3:15])(=[O:3])[CH3:2].[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:15][C@H:5]1[CH2:6][C:7](=[N:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:4]1[C:1](=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6115AnilineHCID 521998p-Toluenesulfonic acid monohydrateHCID 11333160HCID 11333160, compound

Product 1

HCID 11173500HCID 11173500, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (2S)-1-acetyl-2-methyl-2,3-dihydro-4(1H)-quinolinone (20 mg, 0.098 mmol; preparation see Tetrahedron: Asymmetry (1998), 9(7), 1137–1142), aniline (36 μl, 0.394 mmol) and a catalytic amount of p-toluene sulfonic acid monohydrate was refluxed overnight in toluene (4 ml) containing molcular sieve 3 Å (0.9 g). The resulting mixture was filtered, concentrated and purified on silica (ethyl acetate:heptane 1:2) to obtain the sub-titled product (22.8 mg, 0.082 mmol).

Workup

  1. custompreparation
  2. additioncontaining molcular sieve 3 Å (0.9 g)
  3. filtrationThe resulting mixture was filtered
  4. concentrationconcentrated
  5. custompurified on silica (ethyl acetate:heptane 1:2)

Sources & evidence

ORD record
ord-464a240f32894613b4992b6d7f6ee87e
Source dataset
uspto-grants-2006_04
Patent number
US07030246B2

Reaction notes

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