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Sodium Hydroxide → 2-Methyl-4-(3-nitrophenyl)-4,6,7,8-tetrahydro-5(1H)-quinolone

HRID 2209509
Notes
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Reaction equation

HRID 2209509 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[CH2:5][CH2:6][CH2:7][C:8](=[O:24])[C:9]=2[CH:10]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=2)[C:11]=1C(O)=O.CC1NC2CCCC(=O)C=2C(C2C=CC=C([N+]([O-])=O)C=2)C=1C(OCCC#N)=O.[OH-].[Na+]>COCCOC.O>[CH3:1][C:2]1[NH:3][C:4]2[CH2:5][CH2:6][CH2:7][C:8](=[O:24])[C:9]=2[CH:10]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=2)[CH:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 199589032-Methyl-4-(3-nitrophenyl)-5-oxo-1,4,5,6,7,8-hexahydro-3-quinolinecarboxylic acidHCID 199589102-Cyanoethyl 2-methyl-4-(3-nitrophenyl)-5-oxo-1,4,5,6,7,8-hexahydro-3-quinolinecarboxylate

Product 1

HCID 199589342-Methyl-4-(3-nitrophenyl)-4,6,7,8-tetrahydro-5(1H)-quinolone

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 80711,2-DimethoxyethaneSolvent

Procedure

2-Methyl-4-(3-nitrophenyl)-5-oxo-1,4,5,6,7,8-hexahydro-3-quinolinecarboxylic acid. To a suspension of 2-cyanoethyl 2-methyl-4-(3-nitrophenyl)-5-oxo-1,4,5,6,7,8-hexahydro-3-quinolinecarboxylate (0.47 g) in ethylene glycol dimethyl ether (2 mL) was added 1N sodium hydroxide (4 mL). The mixture was stirred for 20 h, during which time all of the solid went into solution. The mixture was diluted with water, washed with ethyl acetate, and acidified by addition of concentrated hydrochloric acid. The resulting precipitate was collected by vacuum filtration and dried to give the acid as a yellow solid (0.31 g); mp 253°-255° C.; MS: 328 (M); NMR: 1.63-2.00 (m,2, CH2), 2.20 (m,2, CH2), 2.31 (s,3, CH3), 2.49 (m,2, CH2), 5.0 (s,1, CH), 7.49-7.61 (m,2, Ar), 7.97 (m,2, Ar), 9.24 (s, 1, NH). Analysis for C17H16N2O5 : Calculated: C, 62.19; H, 4.91; N, 8.53; Found: C, 62.16; H, 5.02; N, 8.33.

Workup

  1. washwashed with ethyl acetate
  2. additionacidified by addition of concentrated hydrochloric acid
  3. filtrationThe resulting precipitate was collected by vacuum filtration
  4. customdried

Sources & evidence

ORD record
ord-4162e36760f54fdfa9883afc050430b8
Source dataset
uspto-grants-1995_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05455253

Reaction notes

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