Water → HCID 15937757, compound

HRID 327454Notes

Reaction equation

HRID 327454 reaction equation
[Br:1]Br.[CH:3]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH:7]([NH:15][CH:16]=[O:17])[CH2:6]1)=[O:4].C([O-])(=O)C.[Na+].O>C(O)(=O)C>[CH:3]([N:5]1[C:14]2[C:9](=[CH:10][C:11]([Br:1])=[CH:12][CH:13]=2)[CH2:8][CH:7]([NH:15][CH:16]=[O:17])[CH2:6]1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 517045Sodium AcetateHCID 15937755HCID 15937755, compound

Product 1

HCID 15937757HCID 15937757, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (10.2 g, 0.064 mol) was added to a stirred solution of N-(1-formyl-1,2,3,4-tetrahydro-3-quinolyl)formamide (14.0 g, 0.065 mol) in acetic acid (70 mL) containing anhydrous sodium acetate (10.2 g, 0.12 mol). The solution was stirred for 30 minutes and water (500 mL) was added. The precipitate was filtered off and air dried to give 15.8 g (86%) of N-(1-formyl-6-bromo-1,2,3,4-tetrahydro-3-quinolyl)formamide, mp 174°-178° C. A sample was recrystallized from ethanol for analysis; mp 178°-181° C.

Workup

  1. filtrationThe precipitate was filtered off
  2. customair dried

Sources & evidence

ORD record
ord-48c06806c77f4688b4c81565300aa9a7
Source dataset
uspto-grants-1993_12
Patent number
US05273975

Reaction notes

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