HCID 178469479, compound → HCID 178524691, compound

HRID 1680534Notes

Reaction equation

HRID 1680534 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[CH2:10][CH2:11][CH2:12][CH:13]([OH:17])[C:14]=2[C:15]=1[OH:16])=[O:5])C>[OH-].[Na+]>[OH:16][C:15]1[C:14]2[CH:13]([OH:17])[CH2:12][CH2:11][CH2:10][C:9]=2[N:8]=[CH:7][C:6]=1[C:4]([OH:5])=[O:3]

Participants

3

Reactant 1

HCID 178469479HCID 178469479, compound

Product 1

HCID 178524691HCID 178524691, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

4,5-Dihydroxy-5,6,7,8-tetrahydroquinoline-3-carboxylic acid ethyl ester (4.7 g) was dissolved in 40 ml of 1 N sodium hydroxide. The resulting solution was stirred on an oil bath at 50° C. for 3 hours and then allowed to stand at room temperature overnight. After the small amount of insoluble matter was removed, the solution was adjusted to pH 2.4 with dilute hydrochloric acid. The precipitate so formed was separated by filtration to obtain a yield of 3.8 g of the desired compound. Its infrared absorption spectrum (KBr tablet) had absorption peaks at 3400, 3060, 2960, 1700, 1650, 1530, and 1510 cm-1, and its n.m.r. spectrum (CF3COOH, 60Mc, TMS) had signals at δ values of 1.8-2.6 (4H, m), 2.9-3.5 (2H, m), 5.55 (1H, bs), and 8.9-9.2 (1H, m).

Workup

  1. waitto stand at room temperature overnight
  2. customAfter the small amount of insoluble matter was removed
  3. customThe precipitate so formed
  4. customwas separated by filtration

Sources & evidence

ORD record
ord-80c690168ff148bcb3026d006b0c7a5c
Source dataset
uspto-grants-1981_06
Patent number
US04273932

Reaction notes

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