Tetrahydrofuran → 2,4,5-Triamino-3-chloro-benzoic acid methyl ester

HRID 2039605Notes

Reaction equation

HRID 2039605 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[C:7]([NH2:13])=[C:6]([Cl:14])[C:5]=1[N:15]=[N+]=[N-].CCO.CO.[NH4+].[Cl-].C1COCC1>C(Cl)Cl.[Zn]>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([NH2:13])=[C:6]([Cl:14])[C:5]=1[NH2:15]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 18681192Ethanol, mixt. with methanolHCID 578559864-Amino-2-azido-3-chloro-5-nitro-benzoic acid methyl ester

Product 1

HCID 578559942,4,5-Triamino-3-chloro-benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4.4 g (16.19 mmol) of 4-amino-2-azido-3-chloro-5-nitro-benzoic acid methyl ester in 161 mL of a mixture EtOH:MeOH 2:1 (v/v), 161 mL of a saturated NH4Cl aqueous solution is added followed by the addition of 88 mL of THF. Then 5.2 g (81 mmol) of powdered zinc is added and the reaction is stirred at ambient temperature during 5 h. The suspension is diluted with CH2Cl2 and the organic phase is washed with brine (2 times) and then dried on Na2SO4. After filtration and evaporation 3.2 g (14.84 mmol, 92%) of a dark violet-red solid were obtained and used directly in the next step without more purification. LC/MS: 216/218 (M+1)+

Workup

  1. additionis added
  2. washthe organic phase is washed with brine (2 times)
  3. customdried on Na2SO4
  4. filtrationAfter filtration
  5. customwere obtained
  6. customused directly in the next step without more purification

Sources & evidence

ORD record
ord-9cad38e399c14b64ac3bfd056e416c57
Source dataset
uspto-grants-2013_11
Patent number
US08580785B2

Reaction notes

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