Acetic Acid → HCID 135838170, compound

HRID 1377049Notes

Reaction equation

HRID 1377049 reaction equation
Br[CH2:2][C:3]1[C:4]2[CH:24]=[CH:23][CH:22]=[CH:21][C:5]=2[C:6]2[C:7](=[O:20])[NH:8][C:9]([NH:13]C(=O)C(C)(C)C)=[N:10][C:11]=2[CH:12]=1.[C:25](O)(=[O:27])C>C[O-].[Na+]>[NH2:13][C:9]1[NH:8][C:7](=[O:20])[C:6]2[C:5]3[CH:21]=[CH:22][CH:23]=[CH:24][C:4]=3[C:3]([CH2:2][O:27][CH3:25])=[CH:12][C:11]=2[N:10]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 135838176HCID 135838176, compound

Product 1

HCID 135838170HCID 135838170, compound

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

Conditions

Temperature
65 °C

Procedure

A solution of N-(6-(bromomethyl)-1,2-dihydro-1-oxobenzo[f]quinazolin-3-yl)pivalamide (0.28 g, 0.72 mmole) in 0.3M sodium methoxide (25 ml) was stirred and heated at 65° C. under a nitrogen atmosphere for 4 hours. After cooling, the mixure was acidified to pH 6 with glacial acetic acid, and then all solvent was removed under reduced pressure. The residue was triturated with water (20 ml), then filtered, washed with water and acetone, and dried to give 3-amino-6-(methoxymethyl)benzo[f]quinazolin-1(2H)-one as an off-white solid. (0.12 g, 58%) 1H NMR (DMSO-d6, 200 MHz) d 3.39(s, 3H, OCH3); 4.85(s, 2H, CH2); 6.54(br s, 2H, NH2); 7.33(s, 1H, Ar); 7.44(dt, J=6.9, 1.4 Hz, 1H, Ar); 7.59(dt, J=6.9, 1.4 Hz, 1H, Ar); 7.96(dd, J=8.2, 1.0 Hz, 1H, Ar); 9.69(d, d=8 Hz, 1H, Ar); 11.11(br s, 1H, NH); 11.91(br s, <1H, pyr-NH+). Anal. Calculated for C14H13N3O2.1/2HOAc.1/10H2O: C, 62.75; H, 5.34; N, 14.64. Found C, 62.74; H, 5.31; N, 14.64.

Workup

  1. temperatureAfter cooling
  2. customall solvent was removed under reduced pressure
  3. customThe residue was triturated with water (20 ml)
  4. filtrationfiltered
  5. washwashed with water and acetone
  6. customdried

Sources & evidence

ORD record
ord-2fd60640df0a4d86937926eca638f13a
Source dataset
uspto-grants-1997_09
Patent number
US05663337

Reaction notes

Loading…