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Acetic Acid → methyl 6-(2,3-dihydro-1H-inden-2-ylamino)-2-methyl-4-phenylquinoline-3-carboxylate

HRID 570383
Notes
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Reaction equation

HRID 570383 reaction equation
CC(O)=O.[NH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([CH3:16])[C:10]([C:17]([O:19][CH3:20])=[O:18])=[C:9]2[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH2:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:29][C:28]1=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[CH2:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:29][CH:28]1[NH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([CH3:16])[C:10]([C:17]([O:19][CH3:20])=[O:18])=[C:9]2[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 119832-IndanoneHCID 5049666Sodium triacetoxyborohydrideHCID 68293887Methyl 6-amino-2-methyl-4-phenylquinoline-3-carboxylate

Product 1

HCID 68294847methyl 6-(2,3-dihydro-1H-inden-2-ylamino)-2-methyl-4-phenylquinoline-3-carboxylateYield 72.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A method of Abdel-Magid et al (J. Org. Chem., 61, 3849, 1996) was used: Glacial AcOH (0.2 ml) was added to a solution of the product of Step 2 (0.91 g, 3.31 mmol), 1H-inden-2(3H)-one (0.41 g, 3.31 mmol) and NaBH(OAc)3 (1.05 g, 4.9 mmol) in anhydrous 1,2-dichloroethane (12.5 ml). The resulting mixture was stirred overnight at room temperature under N2 than quenched by addition of 1N NaOH aq (1 ml). This was diluted to 60 ml with Et2O and washed with N2. The organic phase was dried over anhydrous MgSO4, filtered and filtrate evaporated to dryness under reduced pressure. The residue was purified by flash column chromatography (SiO2, CH2Cl2) to give pure product as a yellow solid (0.98 g, 72%). 1H NMR (300 MHz, CDCl3) δ 7.84 (d, J=9.0 Hz, 1H), 7.34-7.49(m, 5H), 7.15-7.18(m, 4H), 7.07(dd, J=1.7, 9.0 Hz, 1H), 6.49(d, J=1.7 Hz, 1H), 4.11-4.18(m, 2H), 3.55(s, 3H), 3.2(dd, J=6.2, 16 Hz, 2H), 2.8(dd, J=6.2, 16 Hz, 2H), 2.68(s, 3H).

Workup

  1. customthan quenched by addition of 1N NaOH aq (1 ml)
  2. additionThis was diluted to 60 ml with Et2O
  3. washwashed with N2
  4. dry with materialThe organic phase was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. customfiltrate evaporated to dryness under reduced pressure
  7. customThe residue was purified by flash column chromatography (SiO2, CH2Cl2)

Sources & evidence

ORD record
ord-445724af04a74dabb370ba3c8395e1f8
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09023848B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes