Hydrochloric Acid → HCID 53418411, compound

HRID 2274570Notes

Reaction equation

HRID 2274570 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[N:12]([O-])=O.[Na+].[ClH:16]>O>[ClH:16].[Br:11][C:8]1[CH:9]=[CH:10][C:2]([NH:1][NH2:12])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 798582-Amino-5-bromobenzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 53418411HCID 53418411, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 2-amino-5-bromobenzoic acid (50.0 g, 231.5 mmol) in conc. HCl (250 mL) at −10° C. was added a solution of sodium nitrite (23.92 g, 347.2 mmol) in water (250 mL), slowly, followed by stirring for 2 h. To this reaction mixture was slowly added a solution of stannous chloride (130.50 g, 225.6 mmol) in conc. HCl (125 mL) with continued stirring at RT for 12 h. The reaction mixture was filtered, the residue washed with the minimum amount of water and vacuum dried to afford the title compound as and ‘off white’ solid 61 g (100%), which was used for next step without further purification. Rf=0.10 (ethyl acetate); 1H NMR (400 MHz, DMSO-d6): δ 11.60-9.60 (brs, 3H), 7.93 (d, J=2.4 Hz, 1H), 7.72 (dd, J=2.4 & 8.8 Hz, 1H), 7.12 (d, J=8.8 Hz, 1H); ES-MS: m/z 229.1 (M−H).

Workup

  1. stirringwith continued stirring at RT for 12 h
  2. filtrationThe reaction mixture was filtered
  3. washthe residue washed with the minimum amount of water and vacuum
  4. customdried

Sources & evidence

ORD record
ord-05fbf2c6bb5248bcb3f22dc7023b431b
Source dataset
uspto-grants-2015_09
Patent number
US09126980B2

Reaction notes

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