Formaldehyde → HCID 20369935, compound

HRID 1834216Notes

Reaction equation

HRID 1834216 reaction equation
[C:1]([NH:4][C:5]([CH3:24])([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17]C(=O)C)=[C:13]([N+:21]([O-])=O)[CH:12]=1)[C:6]([O:8]C)=[O:7])(=[O:3])[CH3:2].[H][H].C=O.[C:29]([O-])(=O)C.[Na+]>[Ni]>[C:1]([NH:4][C:5]([CH3:24])([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]([NH:21][CH3:29])[CH:12]=1)[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 517045Sodium AcetateHCID 23458801HCID 23458801, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20369935HCID 20369935, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

Methyl 2-acetamido-2-methyl-3-(3-nitro-4-acetamidophenyl)propionate is treated with hydrogen, formaldehyde, sodium acetate and Raney nickel following the procedure of part B of Example 4 to produce 2-acetamido-2-methyl-3(3-methylamino-4-aminophenyl)propionic acid. This product is hydrolyzed with 10% HCl and cyclized with phosgene by the procedure of part B of Example 4 to yield Example 8 title compound.

Sources & evidence

ORD record
ord-960fc9f4f660465bacb65da57d614480
Source dataset
uspto-grants-1978_01
Patent number
US04069333

Reaction notes

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