Methanol → HCID 178525333, compound

HRID 2185192Notes

Reaction equation

HRID 2185192 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:19]=[C:18]([OH:20])[C:17]3[C:12](=[C:13]([CH:24]=O)[CH:14]=[C:15]([N+:21]([O-:23])=[O:22])[CH:16]=3)[N:11]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].C([C:30]([CH:32]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:31])(C)(C)C.C[OH:53]>ClCCl.O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:19]=[C:18]([OH:20])[C:17]3[C:12](=[C:13]([CH:24]=[CH:32][C:30]([OH:53])=[O:31])[CH:14]=[C:15]([N+:21]([O-:23])=[O:22])[CH:16]=3)[N:11]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 887MethanolHCID 3384728HCID 3384728, compoundHCID 178519764HCID 178519764, compound

Product 1

HCID 178525333HCID 178525333, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 2-((3,4-dichlorophenyl)amino)-4-hydroxy-6-nitroquinazoline-8-carbaldehyde (250 mg) and t-butylcarbonylmethylenetriphenylphosphorane (274 mg) in dichloromethane (15 mL) was stirred at room temperature for 3 h. The resulting solution was concentrated and the residue was dissolved in tetrahydrofuran (10 mL). Hydrochloric acid (1 N, 4 mL) was added, and the reaction was stirred at room temperature for 0.5 h. The solution was then evaporated to afford a brown solid, which was suspended in methanol (30 mL) and tetrahydrofuran (3 mL). The product was isolated by filtration, washed with methanol and dried to afford the title compound as a brown solid (71 mg). 1H NMR (300 MHz, DMSO-d6): 8.74 (bd, J=2.1 Hz, 1H), 8.64 (bd, J=1.8 Hz, 1H), 8.23 (m, 2H), 7.54 (m, 2H), 6.80 (d, J=16.2 Hz, 1H). HPLC Method A: 6.13 min. MS (APCI−): m/z 419, 421.

Workup

  1. concentrationThe resulting solution was concentrated
  2. dissolutionthe residue was dissolved in tetrahydrofuran (10 mL)
  3. additionHydrochloric acid (1 N, 4 mL) was added
  4. stirringthe reaction was stirred at room temperature for 0.5 h
  5. customThe solution was then evaporated
  6. customto afford a brown solid, which
  7. customThe product was isolated by filtration
  8. washwashed with methanol
  9. customdried

Sources & evidence

ORD record
ord-90f2a28e703e475aa6af7e97e0f1c4de
Source dataset
uspto-grants-2002_06
Patent number
US06399603B1

Reaction notes

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