Glycolic Acid → HCID 15224455, compound

HRID 396996Notes

Reaction equation

[CH2:1]([NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[CH:8][C:7]=1[N+:16]([O-])=O)[CH2:2][CH2:3][CH3:4].[C:19](O)(=O)[CH2:20][OH:21]>>[CH2:1]([N:5]1[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:16]=[C:19]1[CH2:20][OH:21])[CH2:2][CH2:3][CH3:4]

Participants

Reactant 2

HCID 757Glycolic Acid

HCID 13958330HCID 13958330, compound

Product 1

HCID 15224455HCID 15224455, compoundYield 78.3%

Procedure

Using the general method of Example 1, N-butyl-3-nitro-4-quinolinamine (9.8 g, 0.04 mole, Example 122) was hydrogenated then reacted with glycolic acid (9.1 g, 0.12 mole) to provide 8.0 g of the desired product as a solid. A small sample was recrystallized from ethyl acetate to provide pure material, m.p. 146-149° C. Analysis: Calculated: %C, 70.6; %H, 6.7; %N, 16.5; Found: %C, 70.3; %H, 6.7; %N, 16.3.

Sources & evidence

ORD record: ord-cf6ff029503f4d2a9810dedb4f1752ff
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06608201B2

Reaction notes

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