Hydrochloric Acid → HCID 178490840, compound

HRID 853697

Reaction equation

HRID 853697 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:4]=1[CH2:5][N:6]1[C:10](=[O:11])[CH2:9][CH2:8][C:7]1=[O:12].C[O:20][C:21]([C:23]1[C:28]([C:29](OC)=[O:30])=[CH:27][CH:26]=[CH:25][N:24]=1)=O.[H-].[Na+].Cl>O1CCCC1.CCOCC.CO>[CH3:1][O:2][C:3]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:4]=1[CH2:5][N:6]1[C:7](=[O:12])[C:8]2[C:21]([OH:20])=[C:23]3[C:28]([CH:27]=[CH:26][CH:25]=[N:24]3)=[C:29]([OH:30])[C:9]=2[C:10]1=[O:11]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydride2×HCID 690582,3-Dimethyl 2,3-pyridinedicarboxylateHCID 113910141-(2,4-Dimethoxybenzyl)pyrrolidine-2,5-dione

Product 1

HCID 178490840HCID 178490840, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To 1-(2,4-dimethoxy-benzyl)-pyrrolidine-2,5-dione 299 (1.4 g, 5.6 mmol) and pyridine-2,3-dicarboxylic acid dimethyl ester (1.13 g, 5.8 mmol) dissolved in tetrahydrofuran (60 ml) and methanol (7.0 ml) was added a 60% dispersion of sodium hydride in mineral oil (NaH, 492 mg, 12.3 mmol). The reaction mixture was warmed to 80° C. and kept at 80° C. with stirring overnight. The reaction mixture was placed in an ice bath and titrated to a pH of 4 with 1 M HCl. 200 ml of ether was added and the resulting yellow solid was collected by filtration. The solid was washed twice with ether, twice with water, and dried under high vacuum with heating to provide 7-(2,4-dimethoxy-benzyl)-5,9-dihydroxy-pyrrolo[3,4-g]quinoline-6,8-dione 300 (1.1 g, 52%). 1H NMR (d-DMSO) δ 10.8 (broad, 2H), 9.0 (d, 1H), 8.67 (d, 1H), 7.72 (m, 1H), 6.90 (d, 1H), 6.5 (d, 1H), 6.38 (dd, 1H), 4.58 (s, 2H), 3.76 (s, 3H), 3.66 (s, 3H). MS: 382.1 (M+1)

Workup

  1. customkept at 80° C.
  2. customThe reaction mixture was placed in an ice bath
  3. filtrationthe resulting yellow solid was collected by filtration
  4. washThe solid was washed twice with ether, twice with water
  5. customdried under high vacuum
  6. temperaturewith heating

Sources & evidence

ORD record
ord-7adba5056dd74c53b5a131f5b6310119
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Linked notes

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