Hydrochloric Acid → HCID 86659461, compound

HRID 536424Notes

Reaction equation

HRID 536424 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:5]([NH:12]C=O)([C:6]([OH:8])=[O:7])[CH:4]([N+:15]([O-:17])=[O:16])[CH:3]=1.Cl>O>[NH2:12][C:5]1([C:9]([CH3:11])=[CH:10][C:2]([Br:1])=[CH:3][CH:4]1[N+:15]([O-:17])=[O:16])[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86659462HCID 86659462, compound

Product 1

HCID 86659461HCID 86659461, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-bromo-1-(formyl-amino)-6-methyl-2-nitrobenzoic acid (20 g) (prepared according to US 2004/0167194 A1), concentrated hydrochloric acid (50 ml), and water (150 ml) was heated at 50° C. for 16 h. The reaction mixture was cooled to room temperature, treated ice cold water, and extracted with ethyl acetate (3×50 ml). The combined organic layers were dried over sodium sulfate and concentrated to give 1-amino-4-bromo-6-methyl-2-nitrobenzoic acid (16 g). 1H-NMR (400 MHz, CDCl3): 13.53 (bs, 1H), 7.56 (s, 1H), 7.07 (bs, 2H), 2.20 (s, 3H). LCMS: m/z=272.89 (M−H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. additiontreated ice cold water
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-045de2dc33bb4e88bc0f02e192e96d9e
Source dataset
uspto-grants-2014_10
Patent number
US08859592B2

Reaction notes

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