Hydrochloric Acid → 8-Methylquinazolin-4(1H)-one

HRID 2280993Notes

Reaction equation

HRID 2280993 reaction equation
[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C(O)(=O)C.[CH:16](N)=[NH:17].C(N)=O.Cl>[OH-].[Na+]>[CH3:11][C:10]1[CH:9]=[CH:8][CH:7]=[C:3]2[C:2]=1[N:1]=[CH:16][NH:17][C:4]2=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 713FormamideHCID 781012-Amino-3-methylbenzoic acidHCID 160693Formamidine acetate

Product 1

HCID 1354713008-Methylquinazolin-4(1H)-oneYield 86%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
160 °C

Procedure

2-Amino-3-methylbenzoic acid (100 g, 0.66 mol), formamidine acetate (206 g, 1.98 mol) and formamide (26 mL, 0.6600 mol) were mixed in a 2 L R.B fitted with Mechanical stirrer. The reaction mixture was heated at 160° C. for 16 h. The reaction completion was monitored by LCMS. After completion, the reaction mixture was cooled to was RT and diluted with 2N NaOH solution (300 mL). After stirring at the same temperature for 15 min, the reaction mixture neutralised with 1.5N HCl solution. The solid precipitated was filtered off, washed with ice cold water and dried under vacuum to yield (90 g, 86% yield) of the titled compound as an off white solid. 1H NMR (DMSO-d6, 400 MHz) δ 12.21 (bs, 1H), 8.10 (s, 1H), 7.95-7.93 (dd, J=8.8, 7.9 Hz, 1H), 7.65-7.63 (d, J=7.9 Hz, 1H), 7.39-7.35 (t, J=15.2 Hz, 1H), 2.51 (s, 3H).

Workup

  1. customfitted with Mechanical stirrer
  2. temperatureAfter completion, the reaction mixture was cooled
  3. customto was RT
  4. customThe solid precipitated
  5. filtrationwas filtered off
  6. washwashed with ice cold water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-3156061c456b4568be3fdd50759cf8a4
Source dataset
uspto-grants-2015_09
Patent number
US09139568B2

Reaction notes

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