Acetic Acid → HCID 135838170, compound

HRID 2258655Notes

Reaction equation

HRID 2258655 reaction equation
BrC[CH2:3][C:4]1[C:5]2[CH:25]=[CH:24][CH:23]=[CH:22][C:6]=2[C:7]2[C:8](=[O:21])[NH:9][C:10]([NH:14]C(=O)C(C)(C)C)=[N:11][C:12]=2[CH:13]=1.[C:26](O)(=[O:28])C>C[O-].[Na+]>[NH2:14][C:10]1[NH:9][C:8](=[O:21])[C:7]2[C:6]3[CH:22]=[CH:23][CH:24]=[CH:25][C:5]=3[C:4]([CH2:3][O:28][CH3:26])=[CH:13][C:12]=2[N:11]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 136102828HCID 136102828, compound

Product 1

HCID 135838170HCID 135838170, compound

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

Conditions

Temperature
65 °C

Procedure

A solution of N-(6-(bromoethyl)-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 mixture 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, J=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-25aa981ce36946f3a0b9601aca2ddd96
Source dataset
uspto-grants-1997_08
Patent number
US05661155

Reaction notes

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