Hydrochloric Acid → HCID 9795059, compound

HRID 2392720Notes

Reaction equation

HRID 2392720 reaction equation
[C:1]([CH2:3][C:4]([NH:6][C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([Cl:14])=[CH:9][C:8]=1[N+:15]([O-:17])=O)=[O:5])#[N:2].[OH-].[Na+].Cl>N1C=CC=CC=1.O>[C:1]([C:3]1[C:4](=[O:5])[NH:6][C:7]2[C:8]([N+:15]=1[O-:17])=[CH:9][C:10]([Cl:14])=[C:11]([Cl:13])[CH:12]=2)#[N:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18980352HCID 18980352, compound

Product 1

HCID 9795059HCID 9795059, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a stirred solution of 142 (0.552 g, 2 mmol) in pyridine (4 mL), 1N NaOH (4 mL, 4 mmol) was added. The resulting mixture was stirred for 4 h, then diluted with water (50 mL) and acidified with 2N HCl to pH 2. The precipitated crude product was washed with water, dried on a filter and washed with ether (5×5 mL) to give 0.365 g (72%) of the title compound as an orange solid: mp 294°-296° C. (from EtOH); IR (KBr) 3104, 3048, 2231, 1675, 1623, 1453, 1399 and 1176 cm-1 ; 1H NMR (DMSO-d6) δ7.54 (s, 1H), 8.25 (s, 1H), 12.20 (s, 1H, N--H). HPLC: 95%; HRMS Calcd for C9H3N3O2Cl2 : 254.9602. Found: 254.9604.

Workup

  1. customThe precipitated crude product
  2. washwas washed with water
  3. customdried on
  4. filtrationa filter
  5. washwashed with ether (5×5 mL)

Sources & evidence

ORD record
ord-2972b1a1c87840a7b49dc2e0a4583a63
Source dataset
uspto-grants-1998_09
Patent number
US05801183

Reaction notes

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