Ammonia → HCID 10378439, compound

HRID 2119899Notes

Reaction equation

HRID 2119899 reaction equation
[CH2:1]([N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9](Cl)[C:8]=2[N:7]=[C:6]1[CH2:19][OH:20])[CH2:2][CH2:3][CH3:4].[NH3:21]>CO>[NH2:21][C:9]1[C:8]2[N:7]=[C:6]([CH2:19][OH:20])[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:17]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 15224459HCID 15224459, compound

Product 1

HCID 10378439HCID 10378439, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
160 °C

Procedure

1-Butyl-4-chloro-1H-imidazo[4,5-c]quinoline-2-methanol (2 g, 6.9 mmole, Example 127) was combined with 12 mL of 12% ammonia in methanol and heated in a Parr bomb at 160° C. for about 20 hours. The resulting solid was collected, rinsed with methanol then purified by silica gel chromatography using ethyl acetate/methanol as the eluent. The resulting solid was slurried with ethyl acetate, collected by filtration and dried to provide the desired product, m.p. 223-225° C.

Workup

  1. customThe resulting solid was collected
  2. washrinsed with methanol
  3. customthen purified by silica gel chromatography
  4. filtrationcollected by filtration
  5. customdried

Sources & evidence

ORD record
ord-f88403a8ddb1422180385d926eac1999
Source dataset
uspto-grants-2004_02
Patent number
US06686472B2

Reaction notes

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