Lithium Hydroxide → 8-Amino-5-bromo-1-methyl-1,2,3,4-tetrahydroquinoline-7-carboxylic acid

HRID 925622Notes

Reaction equation

HRID 925622 reaction equation
[NH2:1][C:2]1[C:3]([C:14]([O:16]C)=[O:15])=[CH:4][C:5]([Br:13])=[C:6]2[C:11]=1[N:10]([CH3:12])[CH2:9][CH2:8][CH2:7]2.[Li+].[OH-]>C1COCC1.O>[NH2:1][C:2]1[C:3]([C:14]([OH:16])=[O:15])=[CH:4][C:5]([Br:13])=[C:6]2[C:11]=1[N:10]([CH3:12])[CH2:9][CH2:8][CH2:7]2

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 89188560Methyl 8-amino-5-bromo-1-methyl-1,2,3,4-tetrahydroquinoline-7-carboxylate

Product 1

HCID 891885778-Amino-5-bromo-1-methyl-1,2,3,4-tetrahydroquinoline-7-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
65 °C

Procedure

To a solution of methyl 8-amino-5-bromo-1-methyl-1,2,3,4-tetrahydroquinoline-7-carboxylate (1.40 g, 4.68 mmol) in 2:1 THF/H2O (18 mL) at rt was added LiOH (224 mg, 9.36 mmol). The solution was warmed to 65° C. and stirred for 20 h. The resulting solution was cooled to rt and the THF was removed in vacuo. The aqueous residue remaining was acidified with 1 M aqueous HCl and the resulting tan solid that precipitated was collected by filtration and dried in vacuo to afford 8-amino-5-bromo-1-methyl-1,2,3,4-tetrahydroquinoline-7-carboxylic acid in pure form.

Workup

  1. temperatureThe resulting solution was cooled to rt
  2. customthe THF was removed in vacuo
  3. filtrationthe resulting tan solid that precipitated was collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-e1e53c9a780f4086b0c8e0f5babb93e1
Source dataset
uspto-grants-2016_03
Patent number
US09284312B2

Reaction notes

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