Lithium iodide → HCID 68511710, compound

HRID 641960Notes

Reaction equation

HRID 641960 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][N:7]([C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[CH3:22])[C:16]([OH:18])=[O:17])[C:6]2=[O:23].[Li+].[I-]>N1C(C)=CC(C)=CC=1C.C(OCC)(=O)C>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][N:7]([C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[CH3:22])[C:16]([OH:18])=[O:17])[C:6]2=[O:23]

Participants

5

Reactant 2

HCID 66321Lithium iodideHCID 68603345HCID 68603345, compound

Product 1

HCID 68511710HCID 68511710, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 79532,4,6-TrimethylpyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
195 °C

Procedure

To a suspension of 3-(6-methoxy-4-oxoquinazolin-3(4H)-yl)-4-methylbenzoic acid (8 g) in 2,4,6-collidine (80 ml) was added LiI (6.2 g) and heated to 195° C. for 54 hours. The reaction mixture was cooled to room temperature and diluted with ethyl acetate. The organic phase was washed with water. The aqueous phase was acidified to pH˜1 with 1N HCl and the resultant solid collected by filtration. The solid was dried in vacuo at 60° C. to yield 3-(6-hydroxy-4-oxoquinazolin-3(4H)-yl)-4-methylbenzoic acid (7.2 g); NMR Spectrum: (DMSOd6) 2.14 (s, 3H), 7.33 (m, 1H), 7.48 (d, 1H), 7.56 (d, 1H), 7.62 (d, 1H), 7.91 (s, 1H), 7.97 (d, 1H), 8.12 (s, 1H); Mass Spectrum: M+H+ 297.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe organic phase was washed with water
  3. filtrationthe resultant solid collected by filtration
  4. customThe solid was dried in vacuo at 60° C.

Sources & evidence

ORD record
ord-95a0b10c36d34dab929fb543cdd77c3f
Source dataset
uspto-grants-2010_04
Patent number
US07696215B2

Reaction notes

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