HCID 23346099, compound → HCID 23346115, compound

HRID 1856208Notes

Reaction equation

HRID 1856208 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]([C:9]1[CH:10]=[C:11]2[C:16]3=[C:17]([CH2:19][CH2:20][N:15]3[C:14](=[O:21])[C:13]([N+:22]([O-])=O)=[C:12]2[CH3:25])[CH:18]=1)([OH:8])[C:4]([F:7])([F:6])[F:5]>[Pd]>[F:7][C:4]([F:5])([F:6])[C:3]([C:9]1[CH:10]=[C:11]2[C:16]3=[C:17]([CH2:19][CH2:20][N:15]3[C:14](=[O:21])[C:13]([NH2:22])=[C:12]2[CH3:25])[CH:18]=1)([OH:8])[C:2]([F:27])([F:26])[F:1]

Participants

3

Reactant 1

HCID 23346099HCID 23346099, compound

Product 1

HCID 23346115HCID 23346115, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 3.0 g. (0.0075 mole) of 1,2-dihydro-8-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-6-methyl-5-nitro-4H-pyrrolo[3,2,1-ij]quinolin-4-one, 150 ml. of alcohol, and 0.5 g. of 10% palladium on charcoal is hydrogenated at an initial pressure of 3 atmospheres in a Parr shaker apparatus until uptake is complete. The catalyst is filtered off, and the filtrate is evaporated. Recrystallization of the residue from alcohol gives 1.7 g (62% ) of 1,2-dihydro-8-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)-ethyl]-5-amino-6-methyl-4H-pyrrolo[3,2,1-ij]quinolin-4-one, m.p. 292°-293°.

Workup

  1. additionA mixture of 3.0 g
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate is evaporated
  4. customRecrystallization of the residue from alcohol

Sources & evidence

ORD record
ord-3ff5e57400604735a19cf93450926a63
Source dataset
uspto-grants-1980_08
Patent number
US04218448

Reaction notes

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