Ammonia → HCID 136360177, compound

HRID 1797885Notes

Reaction equation

HRID 1797885 reaction equation
[ClH:1].[C:2]([C:4]1[CH:5]=[C:6]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:25]C(=O)C)=[C:18]([O:21]C(=O)C)[CH:19]=3)[N:14]=[CH:13][N:12]=2)[CH:7]=[CH:8][CH:9]=1)#[CH:3].N>CO>[ClH:1].[C:2]([C:4]1[CH:5]=[C:6]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([OH:25])=[C:18]([OH:21])[CH:19]=3)[N:14]=[CH:13][N:12]=2)[CH:7]=[CH:8][CH:9]=1)#[CH:3]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 16733971HCID 16733971, compound

Product 1

HCID 136360177HCID 136360177, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the hydrochloride salt, 14 (4.2 g, 11.62 mmol) in methanol (30 ml) was added 25% aqueous ammonia (4.73 ml) and the solution was stirred for 4 h. The reaction mass was filtered and the solid was washed with water to give the N-(3-ethynylphenyl)-6,7-dihydroxy-4-quinazolinamine hydrochloride, 15 (3.0 g, 93%) as a brownish yellow solid. 1H NMR (400 MHz, DMSO-d6): 4.2 (s, 1H), 7.10 (s, 1H), 7.17-7.19 (m, 2H), 7.34-7.39 (t, 1H), 7.79 (s, 1H), 7.87-7.89 (d, 1H), 8.05 (s, 1H), 8.45 (s, 1H), 9.4-9.6 (bs. s, 1H). MS (ESI): 278.

Workup

  1. filtrationThe reaction mass was filtered
  2. washthe solid was washed with water

Sources & evidence

ORD record
ord-70702f0944614685891d1bdac5c841ca
Source dataset
uspto-grants-2013_01
Patent number
US08343950B2

Reaction notes

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