Sulfuric Acid → HCID 2794444, compound

HRID 990941Notes

Reaction equation

HRID 990941 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]CC2C=CC(OC)=CC=2)=[C:4]([O:18][CH3:19])[CH:3]=1.[F:20][C:21]([F:31])([F:30])[C:22](=O)[CH2:23][C:24]([O:26]CC)=O.OS(O)(=O)=O>C1C=CC=CC=1>[NH2:8][C:5]1[CH:6]=[C:7]2[C:2](=[CH:3][C:4]=1[O:18][CH3:19])[NH:1][C:24](=[O:26])[CH:23]=[C:22]2[C:21]([F:20])([F:30])[F:31]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 18416154HCID 18416154, compound

Product 1

HCID 2794444HCID 2794444, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

This compound was prepared according to General Method 11 (EXAMPLE 22) from (4-amino-2-methoxyphenyl)-(4-methoxybenzyl)amine (1.23 g, 4.76 mmol) and ethyl 4,4,4-trifluoroacetoacetate (1.05 g, 5.71 mmol) in 60 mL benzene followed by treatment with 10 mL concentrated H2SO4 to afford 0.734 (60%) of 6-amino-7-methoxy-4-(trifluoromethyl)-1H-quinolin-2-one, a yellow solid, after rinsing with MeOH:ether:hexanes. Data for 6-amino-7-methoxy-4-(trifluoromethyl)-1H-quinolin-2-one: Rf 0.28 (19:1 CH2Cl2:MeOH); 1H NMR (500 MHz, CDCl3) δ 12.2 (v broad s, 1H), 7.06 (broad s, 1H), 6.93 (s, 1H), 6.79 (s, 1H), 4.01 (s, 3H), 3.94 (broad s, 2H).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-2b5b17c740de4023b5126bd5145ce14d
Source dataset
uspto-grants-2002_10
Patent number
US06462038B1

Reaction notes

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