Chlorotrimethylsilane → HCID 20551283, compound

HRID 1447290Notes

Reaction equation

HRID 1447290 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10](=[O:17])[C:11](=[CH:15][CH:16]=2)[C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[Si](C)(C)C.Cl[C:31]([O:33][CH3:34])=[O:32]>ClCCl>[CH3:34][O:33][C:31]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:9][C:10](=[O:17])[C:11](=[CH:15][CH:16]=2)[C:12]([OH:14])=[O:13])=[CH:6][CH:7]=1)=[O:32]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 129189566-(4-Aminophenyl)-1,2-dihydro-2-oxonicotinic acid

Product 1

HCID 20551283HCID 20551283, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using the method for the preparation of the side chain acid in Example 3, 4.62 g (20 mmol) of 6-(4-aminophenyl)-1,2-dihydro-2-oxonicotinic acid, 8.4 ml (60 mmol) of triethylamine, 8.0 ml (63 mmol) of chlorotrimethylsilane, 200 ml of dichloromethane, and 2.5 ml (30 mmol) of methyl chloroformate gives 5.04 g of 6-[4-(methoxycarbonylamino)phenyl]-1,2-dihydro-2-oxonicotinic acid.

Sources & evidence

ORD record
ord-98800c8a54a94205ab6e950df5b3e49c
Source dataset
uspto-grants-1982_02
Patent number
US04315858

Reaction notes

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