Aluminum(III) Chloride → Methyl 2-hydroxy-4-(methylamino)-5-nitrobenzoate

HRID 1898327Notes

Reaction equation

HRID 1898327 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]([NH:13][CH3:14])[C:10]([N+:15]([O-:17])=[O:16])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)CCl>[OH:2][C:3]1[CH:12]=[C:11]([NH:13][CH3:14])[C:10]([N+:15]([O-:17])=[O:16])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 67331452Methyl 2-methoxy-4-(methylamino)-5-nitrobenzoate

Product 1

HCID 67502601Methyl 2-hydroxy-4-(methylamino)-5-nitrobenzoateYield 106,533.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The title compound was prepared following the procedure described for Step-5 of Intermediate-1 using methyl 2-methoxy-4-(methylamino)-5-nitrobenzoate (4.00 g, 0.0166 mmol), anhydrous aluminium chloride (6.64 g, 0.0499 mmol) and EDC to afford 4.00 g of crude desired product. 1HNMR (DMSO-d6): δ 2.93 (d, J=5.1 Hz, 3H), 3.86 (s, 3H), 6.28 (s, 1H), 8.48 (bs, 1H), 8.59 (s, 1H), 11.15 (s, 1H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-a340d1cc49bf417781b49ba978a04b2b
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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