Hydrochloric Acid → HCID 178526596, compound

HRID 1592934Notes

Reaction equation

HRID 1592934 reaction equation
[OH:1][C:2]1[C:3]2[C:10](C(O)=O)=[C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1.N#N.Cl>N1C2C(=CC=CC=2)C=CC=1.O>[OH:1][C:2]1[C:3]2[CH:10]=[C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 178524034HCID 178524034, compound

Product 1

HCID 178526596HCID 178526596, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7047QuinolineSolvent

Procedure

18.4 g of 4-hydroxy-6-(3-nitrophenyl)furo[2,3-d]pyrimidine-5-carboxylic acid are placed in ca. 200 ml of quinoline, and heated for 20 min to 200-220° C. under a constant stream of N2. Then, 0.7 g of Cu2O are added. After 2 hours, an additional 0.4 g of Cu2O is added. 1 hour later, another spatula tip of Cu2O is added and the temperature lowered. The next day, the reaction mixture is mixed with 0.5 litres of 2.5 M HCl, diluted with H2O, stirred, left to stand for 8 h and filtered by suction. The residue is washed with conc. ammonia and with a lot of H2O. The basic filtrate is acidified with conc. HCl, filtered by suction and washed with a lot of H2O. The crude product from the two residues is used directly without further working up m.p.: >300° C. IR: 3091 w, 2853w, 1670ss, 1593w, 1527s, 1496w, 1475w, 1373w, 1348s, 1297w, 1202m, 938m, 900m, 783w, 740w, 703w, 622w.

Workup

  1. addition1 hour later, another spatula tip of Cu2O is added
  2. waitleft
  3. waitto stand for 8 h
  4. filtrationfiltered by suction
  5. washThe residue is washed with conc. ammonia and with a lot of H2O
  6. filtrationfiltered by suction
  7. washwashed with a lot of H2O

Sources & evidence

ORD record
ord-4237ed5f782c4e418b3ab862f75e84e6
Source dataset
uspto-grants-2007_11
Patent number
US07294633B2

Reaction notes

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