Ethyl formate → 3-Hydroxymethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid, benzyl ester

HRID 328814Notes

Reaction equation

HRID 328814 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]([C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[CH:8]([CH3:25])[CH2:7][C:6]2=[O:26].[CH:27](OCC)=[O:28].[O-]CC.[Na+].[H-].[Na+]>C1C=CC=CC=1.C(O)C>[OH:28][CH:27]=[C:7]1[C:6](=[O:26])[C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH:8]1[CH3:25]

Participants

7

Reactant 4

HCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 2723922Sodium ethoxideHCID 15480673Benzyl 6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydroquinoline-1-carboxylate

Product 1

HCID 867338553-Hydroxymethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid, benzyl ester

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

Following the procedure of Examples 1-E, 16-B and 17-B, 9.5 g. of benzyl 6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydroquinoline-1-carboxylate, 10.95 ml. of ethyl formate and sodium ethoxide prepared from 2.57 g. of sodium hydride and 3.23 ml. of ethanol in 120 ml. of benzene gave on work-up a yellow oil which on crystallization afforded 6.0 g. of crude product, m.p. 106°-110° C. The analytical same is recrystallized several times from methanol, m.p. 116°-118° C.

Workup

  1. customon crystallization
  2. customafforded 6.0 g
  3. customThe analytical same is recrystallized several times from methanol, m.p. 116°-118° C.

Sources & evidence

ORD record
ord-db58b3f5061145f28d6f1870dd77da35
Source dataset
uspto-grants-1977_04
Patent number
US04018758

Reaction notes

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