Bromine → Methyl 8-amino-5-bromo-1-methyl-1,2,3,4-tetrahydroquinoline-7-carboxylate

HRID 925621Notes

Reaction equation

HRID 925621 reaction equation
[NH2:1][C:2]1[C:3]([C:13]([O:15][CH3:16])=[O:14])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]([CH3:12])[CH2:9][CH2:8][CH2:7]2.[Br:17]Br>C(Cl)Cl>[NH2:1][C:2]1[C:3]([C:13]([O:15][CH3:16])=[O:14])=[CH:4][C:5]([Br:17])=[C:6]2[C:11]=1[N:10]([CH3:12])[CH2:9][CH2:8][CH2:7]2

Participants

4

Reactant 2

HCID 24408BromineHCID 89188582Methyl 8-amino-1-methyl-1,2,3,4-tetrahydroquinoline-7-carboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 8-amino-1-methyl-1,2,3,4-tetrahydroquinoline-7-carboxylate (1.05 g, 4.77 mmol) in CH2Cl2 (19 mL) at 0° C. was added Br2 (1.0 M in CH2Cl2, 4.77 mL, 4.77 mmol). The mixture was warmed slowly to rt and stirred at rt for 20 min. The resulting solution was quenched with 10% aqueous Na2S2O3 (1 mL), basified with 10% aqueous Na2CO3, and extracted with CH2Cl2. The combined extracts were dried (Na2SO4) and concentrated to afford methyl 8-amino-5-bromo-1-methyl-1,2,3,4-tetrahydroquinoline-7-carboxylate in pure form.

Workup

  1. customThe resulting solution was quenched with 10% aqueous Na2S2O3 (1 mL)
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a115cd8b24834f41abfc31628b6636fc
Source dataset
uspto-grants-2016_03
Patent number
US09284312B2

Reaction notes

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