HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Sodium Carbonate → 4-(1-Acetyl-1,2,3,4-tetrahydroquinolin-6-yl)-3-methylbenzoic acid

HRID 1870893
Notes
Print preview

Reaction equation

HRID 1870893 reaction equation
B([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]=1[CH3:13])(O)O.[C:14]([N:17]1[C:26]2[C:21](=[CH:22][C:23](OS(C(F)(F)F)(=O)=O)=[CH:24][CH:25]=2)[CH2:20][CH2:19][CH2:18]1)(=[O:16])[CH3:15].[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+]>O.C(COC)OC>[C:14]([N:17]1[C:26]2[C:21](=[CH:22][C:23]([C:4]3[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]=3[CH3:13])=[CH:24][CH:25]=2)[CH2:20][CH2:19][CH2:18]1)(=[O:16])[CH3:15]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 186942601-Acetyl-1,2,3,4-tetrahydro-6-trifluoromethanesulphonyloxyquinolineHCID 221158924-Borono-3-methylbenzoic acid

Product 1

HCID 186942454-(1-Acetyl-1,2,3,4-tetrahydroquinolin-6-yl)-3-methylbenzoic acidYield 104%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

4-Borono-3-methylbenzoic acid (D29) (220 mg, 1.2 mmol), 1-acetyl-1,2,3,4-tetrahydro-6-trifluoromethanesulphonyloxyquinoline (D41, 410 mg, 1.25 mmol), lithium chloride (150 mg, 3.6 mmol) and sodium carbonate (505 mg, 4.7 mmol) were dissolved in a mixture of water (10 ml) and dimethoxyethane (10 ml). The suspension was degassed with argon for 15 mins and then treated with tetrakis (triphenylphosphine)palladium (O) (68 mg). The reaction mixture was heated at reflux for 28 hrs, then concentrated in vacuo. The residue was treated with 10% aqueous Na2CO3 solution and washed with ethyl acetate. The aqueous layer was acidified with 5M HCl and the resultant precipitate was filtered off and dried to afford the title compound as a light brown solid (386 mg, 100%).

Workup

  1. customThe suspension was degassed with argon for 15 mins
  2. additiontreated with tetrakis (triphenylphosphine)palladium (O) (68 mg)
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux for 28 hrs
  5. concentrationconcentrated in vacuo
  6. additionThe residue was treated with 10% aqueous Na2CO3 solution
  7. washwashed with ethyl acetate
  8. filtrationthe resultant precipitate was filtered off
  9. customdried

Sources & evidence

ORD record
ord-4ebc3f3663be43f89f1996dc74814d80
Source dataset
uspto-grants-2000_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06100272

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes