Hydrochloric Acid → 2-Amino-5-bromobenzoic acid

HRID 2068586

Reaction equation

HRID 2068586 reaction equation
C([NH:4][C:5]1[C:6](=[CH:10][C:11]([Br:14])=[CH:12][CH:13]=1)[C:7]([OH:9])=[O:8])(=O)C.Cl>O1CCOCC1>[Br:14][C:11]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([NH2:4])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 5209352-Acetamido-5-bromobenzoic Acid

Product 1

HCID 798582-Amino-5-bromobenzoic acidYield 91.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of 9 (71 g, 0.275 mol) in 1,4-dioxane (400 mL) was added HCl (400 mL). The mixture was refluxed for 4 h at 110° C. Then the mixture was concentrated and added to 300 mL water. The mixture was filtered and the pH was adjusted to 6 with 2N NaOH, washed with water and dried to give 10 as a white solid (54.5 g, yield: 91.7%).

Workup

  1. concentrationThen the mixture was concentrated
  2. additionadded to 300 mL water
  3. filtrationThe mixture was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-fa5d04b685f14e48a922b9a0d012d30c
Source dataset
uspto-grants-2012_10
Patent number
US08299023B2

Linked notes

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