3-Chloro-2-methyl-1-propene → HCID 67502740, compound

HRID 1898328Notes

Reaction equation

HRID 1898328 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([NH:12][CH3:13])[C:9]([N+:14]([O-:16])=[O:15])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH2:17](Cl)[C:18](=[CH2:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:19][C:18](=[CH2:17])[CH2:20][O:1][C:2]1[CH:11]=[C:10]([NH:12][CH3:13])[C:9]([N+:14]([O-:16])=[O:15])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium CarbonateHCID 67502601Methyl 2-hydroxy-4-(methylamino)-5-nitrobenzoate

Product 1

HCID 67502740HCID 67502740, compoundYield 70,952.602%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared following the procedure described for Step-6 of Intermediate-1 using methyl 2-hydroxy-4-(methylamino)-5-nitrobenzoate (4.00 g, 0.0176 mmol), methallyl chloride (2.8 g, 0.0318 mmol), potassium carbonate (4.38 g, 0.037 mmol) and DMF (50.0 mL) to afford 3.500 g of desired product. 1HNMR (DMSO-d6): δ 1.81 (s, 3H), 3.00 (d, J=4.8 Hz, 3H), 3.76 (s, 3H), 4.65 (s, 2H), 5.00 (s, 1H), 5.24 (s, 1H), 6.30 (s, 1H), 8.59 (s, 2H); [M+H]+: 281.00.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-fb66b5b8a7fc48c58102288bf6e4c358
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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