Hydrochloric Acid → Methyl 4,5-diamino-2-hydroxybenzoate

HRID 1898340Notes

Reaction equation

HRID 1898340 reaction equation
[NH2:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([OH:15])[CH:3]=1.Cl>CO.[Fe]>[NH2:1][C:2]1[C:11]([NH2:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([OH:15])[CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 13912872Methyl 4-amino-2-hydroxy-5-nitrobenzoate

Product 1

HCID 67504371Methyl 4,5-diamino-2-hydroxybenzoateYield 116.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 4-amino-2-hydroxy-5-nitrobenzoate (step 5 of intermediate-1) (0.500 g, 2.35 mmol) in methanol (15.0 mL), iron powder (0.646 g, 11.7 mmol) was added with conc. HCl (5 mL). The reaction mass was refluxed for 2 h. Methanol was removed under vacuum and then water was added. The reaction mass was basified with Na2CO3 and extracted with DCM. The organic layer was dried over anhydrous sodium sulphate and concentrated to afford 0.500 g of the desired product. 1HNMR (DMSO-d6): δ 3.76 (s, 3H), 4.29 (s, 2H), 5.64 (s, 2H), 6.01 (s, 1H), 6.89 (s, 1H), 10.28 (s, 1H).

Workup

  1. temperatureThe reaction mass was refluxed for 2 h
  2. customMethanol was removed under vacuum
  3. additionwater was added
  4. extractionextracted with DCM
  5. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e7c7790e437c46af943f80ef656c9e63
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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