Ammonium Chloride → 1013117-35-5

HRID 2405758Notes

Reaction equation

HRID 2405758 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N+:12]([O-])=O)[N:8]=[CH:7][NH:6][C:5]2=[O:15].[NH4+].[Cl-]>CO.O.[Fe]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[NH2:12])[N:8]=[CH:7][NH:6][C:5]2=[O:15]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 135767899HCID 135767899, compound

Product 1

HCID 1360138721013117-35-5Yield 100.7%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

To a suspension of 6-chloro-7-nitroquinazoline-4-one (7.5 g, 33 mmol) in MeOH (250 mL) was added NH4Cl (17.7 g, 0.33 mol) dissolved in water (75 mL). Iron powder (18.5 g, 330 mmol) was added and the suspension was heated at 65° C. for 2 h. The warm reaction mixture was filtered over diatomaceous earth and washed several times with THF (1 L) and methanol (500 mL). The filtrate was concentrated, washed with water and dried under vacuum at 50° C. to afford the title compound (6.5 g, 90%) as a brown solid. ESI-MS m/z 196 [C8H6ClN3O+H]+.

Workup

  1. customThe warm reaction mixture
  2. filtrationwas filtered over diatomaceous earth
  3. washwashed several times with THF (1 L) and methanol (500 mL)
  4. concentrationThe filtrate was concentrated
  5. washwashed with water
  6. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-a111bca80fd34374af0fd0545523b698
Source dataset
uspto-grants-2014_08
Patent number
US08809326B2

Reaction notes

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